A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction
[Display omitted] •The total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids, was carry out in three steps and high yields.•The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium.•This protocol is compatible with chiral aldehydes. The present study...
Saved in:
| Published in | Tetrahedron letters Vol. 58; no. 33; pp. 3311 - 3315 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
16.08.2017
Elsevier |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | [Display omitted]
•The total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids, was carry out in three steps and high yields.•The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium.•This protocol is compatible with chiral aldehydes.
The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields. |
|---|---|
| AbstractList | The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (+/-)-galipinine, (+/-)-cuspareine, (+/-)-galipeine and (+/-)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields. (C) 2017 Elsevier Ltd. All rights reserved. [Display omitted] •The total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids, was carry out in three steps and high yields.•The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium.•This protocol is compatible with chiral aldehydes. The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields. |
| Author | de Souza Dias, Gabriel Nunes Diaz-Muñoz, Gaspar Isidorio, Raquel Geralda Miranda, Izabel Luzia Diaz, Marisa Alves Nogueira |
| Author_xml | – sequence: 1 givenname: Gaspar surname: Diaz-Muñoz fullname: Diaz-Muñoz, Gaspar email: gaspardm@qui.ufmg.br organization: Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil – sequence: 2 givenname: Raquel Geralda surname: Isidorio fullname: Isidorio, Raquel Geralda organization: Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil – sequence: 3 givenname: Izabel Luzia surname: Miranda fullname: Miranda, Izabel Luzia organization: Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil – sequence: 4 givenname: Gabriel Nunes surname: de Souza Dias fullname: de Souza Dias, Gabriel Nunes organization: Aquaculture-Veterinay School, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil – sequence: 5 givenname: Marisa Alves Nogueira surname: Diaz fullname: Diaz, Marisa Alves Nogueira organization: Department of Biochemistry and Molecular Biology, Universidade Federal de Viçosa, Minas Gerais 36570-900, Brazil |
| BookMark | eNqNkE1r3DAQhkVJoZu0_6AH3YO3Y1u27EshLPkoBHpJ6VHI0ig7W0dKJG3D3vrTK3dDjiViQHN4n1fiOWUnPnhk7HMN6xrq_stunTHPmNcN1HINZYR4x1b1INuq7Yb6hK0ABFQC2vEDO01pB-X0A6zYnwtugjeUkGtvOTpHhtBnng4-bzFR4sHxUh_19mBjeNqTDzP5Ep9_6TmQTXyfyN_zkuaPW12KStYnh5E_oCWd0fKflDPd8zCjI68zBc8jarMsH9l7p-eEn17uM_bj6vJuc1Pdfr_-trm4rUwLfa4GB-0kXG_tIJ0UKLoG-nGY-q6zVjYjiqmXph1lB_UgeiOcbUQzyslY6UqsPWPi2GtiSCmiU4-RHnQ8qBrUYlHt1NGiWiwqKCNEwc6P2DNOwaXFjcFXFBatsisvla3pSnp4e3pD-Z-KTdj7XNCvRxSLhN-EUb3gliKarGyg___0L43hozw |
| CitedBy_id | crossref_primary_10_1039_C8CC10309G crossref_primary_10_1021_acs_jnatprod_8b00672 crossref_primary_10_1002_ejoc_201900493 crossref_primary_10_1021_acs_orglett_0c01874 crossref_primary_10_1021_acscatal_8b01220 crossref_primary_10_1055_a_1984_9689 |
| Cites_doi | 10.1021/jo900917q 10.1021/jo902424m 10.1002/anie.200600191 10.1080/00397910600773684 10.1021/ja2023042 10.1039/b822822a 10.3762/bjoc.11.99 10.1016/j.tet.2008.06.073 10.1021/jo070665k 10.1021/ja2092954 10.1021/jo0708137 10.1002/ejoc.200800512 10.1039/c5ra05987a 10.1002/chem.200801480 10.1021/ja0353762 10.1021/jo801767n 10.1016/j.tetlet.2012.12.122 10.1002/anie.200503073 10.1021/ol200625h 10.1016/S0040-4020(03)00915-3 10.1016/j.tetasy.2004.12.022 10.1002/ejoc.201100981 10.1021/ja065015x 10.1039/c2ob25122a 10.1039/C5RA05987A 10.1080/00304948.2015.1025012 10.1055/s-2002-19869 10.1016/S0040-4020(01)93261-2 10.1016/S0031-9422(99)00032-1 10.5012/bkcs.2006.27.5.631 10.1002/cjoc.20040220911 10.2174/138527211794518925 10.1055/s-2006-957578 10.1002/jlac.19535800107 10.1021/ja00704a052 |
| ContentType | Journal Article |
| Copyright | 2017 Elsevier Ltd |
| Copyright_xml | – notice: 2017 Elsevier Ltd |
| DBID | 1KM 1KN BLEPL DTL GYRTJ AAYXX CITATION |
| DOI | 10.1016/j.tetlet.2017.07.044 |
| DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2017 CrossRef |
| DatabaseTitle | Web of Science CrossRef |
| DatabaseTitleList | Web of Science |
| Database_xml | – sequence: 1 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1873-3581 |
| EndPage | 3315 |
| ExternalDocumentID | 10_1016_j_tetlet_2017_07_044 000407524200025 S0040403917308900 |
| GrantInformation_xml | – fundername: FAPEMIG; Fundacao de Amparo a Pesquisa do Estado de Minas Gerais (FAPEMIG) grantid: APQ-01061-14 – fundername: PRPq-UFMG |
| GroupedDBID | --- --K --M -ET -~X .~1 0R~ 123 1B1 1RT 1~. 1~5 4.4 457 4G. 53G 5VS 7-5 71M 85S 8P~ 9JM 9JN AABNK AACTN AAEDT AAEDW AAIAV AAIKJ AAKOC AALRI AAOAW AAQFI AARLI AATCM AAXUO ABFNM ABFRF ABGSF ABJNI ABMAC ABPPZ ABUDA ABYKQ ABZDS ACBEA ACDAQ ACGFS ACNCT ACRLP ADBBV ADECG ADEZE ADUVX AEBSH AEFWE AEHWI AEKER AENEX AFKWA AFTJW AFXIZ AFZHZ AGHFR AGUBO AGYEJ AHHHB AIEXJ AIKHN AITUG AJBFU AJOXV AJSZI ALCLG ALMA_UNASSIGNED_HOLDINGS AMFUW AMRAJ AXJTR BKOJK BLXMC CS3 DOVZS DU5 EBS EFJIC EFLBG EJD EO8 EO9 EP2 EP3 F5P FDB FIRID FLBIZ FNPLU FYGXN G-Q GBLVA IH2 J1W K-O KOM M2Z M41 MO0 N9A O-L O9- OAUVE OGGZJ OZT P-8 P-9 P2P PC. Q38 RIG RNS ROL RPZ SCC SDF SDG SDP SES SPC SPCBC SSK SSP SSU SSZ T5K TN5 TWZ WH7 XPP XSW YK3 YR2 ZMT ~02 ~G- ~KM 1KM 1KN AAHBH AAXKI AKRWK BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED .GJ .HR 186 29Q 3EH 6TJ AAQXK AAYOK AAYXX ABDPE ABXDB ACBNA ACKIV ACNNM ACRPL ADMUD ADNMO ADVLN AFFNX AFJKZ AGRDE ASPBG AVWKF AZFZN CITATION D0S FEDTE FGOYB HMS HVGLF HZ~ IHE MVM OHT R2- SCB SEW SOC UQL WUQ XJT Y6R YQJ ZCG ZKB ZXP |
| ID | FETCH-LOGICAL-c306t-8f03b4f6dd87f74e4520698b655dd729e4b67c397501846c4fd24297bcd7f8b63 |
| IEDL.DBID | AIKHN |
| ISICitedReferencesCount | 11 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000407524200025 |
| ISSN | 0040-4039 |
| IngestDate | Fri Dec 06 05:01:25 EST 2024 Tue Sep 17 23:43:37 EDT 2024 Fri Dec 13 17:27:21 EST 2024 Fri Feb 23 02:29:07 EST 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 33 |
| Keywords | Wittig reaction Galipea officinalis Phase transfer medium Tetrahydroquinoline alkaloids ASYMMETRIC-SYNTHESIS QUINOLINES ALLYLIC AMINATION ANGUSTUREINE GALIPININE (+)-ANGUSTUREINE (+)-(S)-ANGUSTUREINE GALIPEA-OFFICINALIS HIGHLY ENANTIOSELECTIVE HYDROGENATION ESTERS |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c306t-8f03b4f6dd87f74e4520698b655dd729e4b67c397501846c4fd24297bcd7f8b63 |
| ORCID | 0000-0002-2923-0235 |
| PageCount | 5 |
| ParticipantIDs | webofscience_primary_000407524200025CitationCount webofscience_primary_000407524200025 elsevier_sciencedirect_doi_10_1016_j_tetlet_2017_07_044 crossref_primary_10_1016_j_tetlet_2017_07_044 |
| PublicationCentury | 2000 |
| PublicationDate | 2017-08-16 |
| PublicationDateYYYYMMDD | 2017-08-16 |
| PublicationDate_xml | – month: 08 year: 2017 text: 2017-08-16 day: 16 |
| PublicationDecade | 2010 |
| PublicationPlace | OXFORD |
| PublicationPlace_xml | – name: OXFORD |
| PublicationTitle | Tetrahedron letters |
| PublicationTitleAbbrev | TETRAHEDRON LETT |
| PublicationYear | 2017 |
| Publisher | Elsevier Ltd Elsevier |
| Publisher_xml | – name: Elsevier Ltd – name: Elsevier |
| References | Wu, Yue, El-Batta, Jiang, Zhao, Annes, Cooksy, Bergdahl (b0035) 2006; 36 Corey, Yamamoto (b0045) 1970; 92 Taber, Sheth (b0060) 2008; 73 Jacquemond-Collet, Benoit-Vical, Valentin, Stanislas, Mallie, Fouraste (b0025) 2002; 68 Nagaoka, Kishi (b0055) 1981; 37 Mester (b0020) 1973; 44 Karatholuvhu, Sinclair, Newton, Alcaraz, Stockman, Fuchs (b0050) 2006; 128 Diaz-Muñoz, Dudley (b0005) 2015; 47 Rakotoson, Fabre, Jacquemond-Collet, Hannedouche, Fourasté, Moulis (b0015) 1998; 64 Jacquemond-Collet, Hannedouche, Fabre, Fourast, Moulis (b0010) 1999; 51 Wang, Lu, Yang, Han, Zhou, Avemaria, Vanderheiden, Braese, Lin, Li, Ma, Theeraladanon, Arisawa, Nakagawa, Wang, Han, Zhou, Rueping, Antonchick, Theissmann, Ryu, Patil, Wu, Yamamoto, O’Byrne, Evans, Shahane, Louafi, Moreau, Fustero, Moscardó, Jiménez, Pérez-Carrión, Sánchez-Roselló, del Pozo, Wang, Zhou, Wang, He, Fan, Kothandaraman, Foo, Chan, Chen, Wang, Lin, Cruz-Lopez, Nunez, Conejo-Garcia, Kimatrai, Campos, Bentley, Davies, Lee, Roberts, Thomson, Wang, Zhuo, Li, Satyanarayana, Pflästerer, Helmchen, Ye, He, Liu, Dai, Helmchen, You, Taylor, Goldberg, Hii, Tummatorn, Diaz-Muñoz, Dudley, Dousová, Horák, Ruzicková, Simunek, Garg, Gahalawat, Pandey (b0030) 2003; 125 Wittig, Geissler (b0040) 1953; 580 Lin, XF (WOS:000223842000011) 2004; 22 Diaz-Munoz, G (000407524200025.1) 2015; 47 Rakotoson, JH (WOS:000077915200021) 1998; 64 Shahane, S (WOS:000259944100013) 2008; 2008 Wu, JL (WOS:000241184900002) 2006; 36 Satyanarayana, G (WOS:000297205800007) 2011; 2011 Rueping, M (WOS:000238068000026) 2006; 45 Avemaria, F (WOS:000184960000008) 2003; 59 Tummatorn, J (WOS:000315321600033) 2013; 54 Wang, TL (WOS:000292439700044) 2011; 133 Wang, WB (WOS:000185012800027) 2003; 125 Karatholuvhu, MS (WOS:000240795000034) 2006; 128 MESTER I (BCI:BCI197559015918) 1973; 44 Lu, SM (WOS:000236506000020) 2006; 45 O'Byrne, A (WOS:000258411600005) 2008; 64 Ryu, JS (WOS:000238241700002) 2006; 27 Ye, KY (WOS:000297398900072) 2011; 133 Patil, NT (WOS:000248793400032) 2007; 72 Dousova, H (WOS:000355166200001) 2015; 11 COREY, EJ (WOS:A1970F100100052) 1970; 92 Wang, ZJ (WOS:000266767400005) 2009; 11 Jacquemond-Collet, I (WOS:000173857600015) 2002; 68 Garg, Y (WOS:000354201500006) 2015; 5 Jacquemond-Collet, I (WOS:000081820200040) 1999; 51 Bentley, SA (WOS:000290465800009) 2011; 13 Taylor, LL (WOS:000304097000015) 2012; 10 Fustero, S (WOS:000261074800010) 2008; 14 Chen, BL (WOS:000273982900050) 2010; 75 NAGAOKA, H (WOS:A1981MT84600001) 1981; 37 Theeraladanon, C (WOS:000227266700010) 2005; 16 Cruz-Lopez, O (WOS:000288985500008) 2011; 15 WITTIG, G (WOS:A1953XV09400006) 1953; 580 Taber, DF (WOS:000259973900025) 2008; 73 El-Batta, A (WOS:000247612200027) 2007; 72 Kothandaraman, P (WOS:000268907300021) 2009; 74 Shahane (10.1016/j.tetlet.2017.07.044_h0075) 2008 Garg (10.1016/j.tetlet.2017.07.044_h0140) 2015; 5 Ryu (10.1016/j.tetlet.2017.07.044_h0060) 2006; 27 Nagaoka (10.1016/j.tetlet.2017.07.044_b0055) 1981; 37 Jacquemond-Collet (10.1016/j.tetlet.2017.07.044_b0025) 2002; 68 Theeraladanon (10.1016/j.tetlet.2017.07.044_h0045) 2005; 16 Taylor (10.1016/j.tetlet.2017.07.044_h0125) 2012; 10 Diaz-Muñoz (10.1016/j.tetlet.2017.07.044_b0005) 2015; 47 Wang (10.1016/j.tetlet.2017.07.044_h0030) 2003; 125 O’Byrne (10.1016/j.tetlet.2017.07.044_h0070) 2008; 64 Wang (10.1016/j.tetlet.2017.07.044_h0085) 2009; 11 Fustero (10.1016/j.tetlet.2017.07.044_h0080) 2008; 14 Jacquemond-Collet (10.1016/j.tetlet.2017.07.044_b0010) 1999; 51 Karatholuvhu (10.1016/j.tetlet.2017.07.044_b0050) 2006; 128 Kothandaraman (10.1016/j.tetlet.2017.07.044_h0090) 2009; 74 Wang (10.1016/j.tetlet.2017.07.044_h0110) 2011; 133 Patil (10.1016/j.tetlet.2017.07.044_h0065) 2007; 72 Mester (10.1016/j.tetlet.2017.07.044_b0020) 1973; 44 Avemaria (10.1016/j.tetlet.2017.07.044_h0035) 2003; 59 Cruz-Lopez (10.1016/j.tetlet.2017.07.044_h0100) 2011; 15 Satyanarayana (10.1016/j.tetlet.2017.07.044_h0115) 2011 Rueping (10.1016/j.tetlet.2017.07.044_h0055) 2006; 45 Wittig (10.1016/j.tetlet.2017.07.044_b0040) 1953; 580 Tummatorn (10.1016/j.tetlet.2017.07.044_h0130) 2013; 54 Wu (10.1016/j.tetlet.2017.07.044_h0145) 2006; 36 El-Batta (10.1016/j.tetlet.2017.07.044_h0150) 2007; 72 Rakotoson (10.1016/j.tetlet.2017.07.044_b0015) 1998; 64 Wang (10.1016/j.tetlet.2017.07.044_h0050) 2006; 45 Bentley (10.1016/j.tetlet.2017.07.044_h0105) 2011; 13 Chen (10.1016/j.tetlet.2017.07.044_h0095) 2010; 75 Dousová (10.1016/j.tetlet.2017.07.044_h0135) 2015; 11 Ye (10.1016/j.tetlet.2017.07.044_h0120) 2011; 133 Taber (10.1016/j.tetlet.2017.07.044_b0060) 2008; 73 Corey (10.1016/j.tetlet.2017.07.044_b0045) 1970; 92 Lin (10.1016/j.tetlet.2017.07.044_h0040) 2004; 22 |
| References_xml | – volume: 580 start-page: 44 year: 1953 end-page: 57 ident: b0040 publication-title: Liebigs Ann contributor: fullname: Geissler – volume: 44 start-page: 123 year: 1973 end-page: 152 ident: b0020 publication-title: Fitoterapia contributor: fullname: Mester – volume: 47 start-page: 179 year: 2015 end-page: 206 ident: b0005 publication-title: Org Prep Proced Int contributor: fullname: Dudley – volume: 37 start-page: 3873 year: 1981 end-page: 3888 ident: b0055 publication-title: Tetrahedron contributor: fullname: Kishi – volume: 51 start-page: 1167 year: 1999 end-page: 1169 ident: b0010 publication-title: Phytochemistry contributor: fullname: Moulis – volume: 92 start-page: 226 year: 1970 end-page: 228 ident: b0045 publication-title: J Am Chem Soc contributor: fullname: Yamamoto – volume: 73 start-page: 8030 year: 2008 end-page: 8032 ident: b0060 publication-title: J Org Chem contributor: fullname: Sheth – volume: 64 start-page: 762 year: 1998 end-page: 763 ident: b0015 publication-title: Planta Med contributor: fullname: Moulis – volume: 128 start-page: 12656 year: 2006 end-page: 12657 ident: b0050 publication-title: J Am Chem Soc contributor: fullname: Fuchs – volume: 68 start-page: 68 year: 2002 end-page: 69 ident: b0025 publication-title: Planta Med contributor: fullname: Fouraste – volume: 36 start-page: 2939 year: 2006 end-page: 2947 ident: b0035 publication-title: Synth Commun contributor: fullname: Bergdahl – volume: 125 start-page: 10536 year: 2003 end-page: 10537 ident: b0030 article-title: Nishida A publication-title: J Am Chem Soc contributor: fullname: Pandey – volume: 580 start-page: 44 year: 1953 ident: WOS:A1953XV09400006 article-title: *ZUR REAKTIONSWEISE DES PENTAPHENYL-PHOSPHORS UND EINIGER DERIVATE publication-title: ANNALEN DER CHEMIE-JUSTUS LIEBIG contributor: fullname: WITTIG, G – volume: 74 start-page: 5947 year: 2009 ident: WOS:000268907300021 article-title: Gold-Catalyzed Intramolecular Allylic Amination of 2-Tosylaminophenylprop-1-en-3-ols. A Concise Synthesis of (+/-)-Angustureine publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo900917q contributor: fullname: Kothandaraman, P – volume: 92 start-page: 226 year: 1970 ident: WOS:A1970F100100052 article-title: MODIFICATION OF WITTIG REACTION TO PERMIT STEREOSPECIFIC SYNTHESIS OF CERTAIN TRISUBSTITUTED OLEFINS . STEREOSPECIFIC SYNTHESIS OF ALPHA-SANTALOL publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: COREY, EJ – volume: 75 start-page: 941 year: 2010 ident: WOS:000273982900050 article-title: Highly Diastereoselective Addition of Alkynylmagnesium Chlorides to N-tert-Butanesulfinyl Aldimines: A Practical and General Access to Chiral alpha-Branched Amines publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo902424m contributor: fullname: Chen, BL – volume: 27 start-page: 631 year: 2006 ident: WOS:000238241700002 article-title: Hydroarylation for the facile synthesis of 2-substituted tetrahydroquinoline: A concise synthesis of (+)-(S)-angustureine publication-title: BULLETIN OF THE KOREAN CHEMICAL SOCIETY contributor: fullname: Ryu, JS – volume: 22 start-page: 932 year: 2004 ident: WOS:000223842000011 article-title: Total synthesis of tetrahydroquinoline alkaloid (+)-angustureine publication-title: CHINESE JOURNAL OF CHEMISTRY contributor: fullname: Lin, XF – volume: 44 start-page: 123 year: 1973 ident: BCI:BCI197559015918 article-title: THE OCCURRENCE OF THE ALKALOIDS IN RUTACEAE publication-title: Fitoterapia contributor: fullname: MESTER I – volume: 45 start-page: 3683 year: 2006 ident: WOS:000238068000026 article-title: A highly enantioselective bronsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200600191 contributor: fullname: Rueping, M – volume: 36 start-page: 2939 year: 2006 ident: WOS:000241184900002 article-title: One-pot Wittig reactions in aqueous media: A rapid and environmentally benign synthesis of alpha,beta-unsaturated carboxylic esters and nitriles publication-title: SYNTHETIC COMMUNICATIONS doi: 10.1080/00397910600773684 contributor: fullname: Wu, JL – volume: 133 start-page: 9878 year: 2011 ident: WOS:000292439700044 article-title: Highly Enantioselective Hydrogenation of Quinolines Using Phosphine-Free Chiral Cationic Ruthenium Catalysts: Scope, Mechanism, and Origin of Enantioselectivity publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja2023042 contributor: fullname: Wang, TL – volume: 11 start-page: 767 year: 2009 ident: WOS:000266767400005 article-title: Highly enantioselective hydrogenation of quinolines under solvent-free or highly concentrated conditions publication-title: GREEN CHEMISTRY doi: 10.1039/b822822a contributor: fullname: Wang, ZJ – volume: 11 start-page: 884 year: 2015 ident: WOS:000355166200001 article-title: An intramolecular C-N cross-coupling of beta-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis publication-title: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY doi: 10.3762/bjoc.11.99 contributor: fullname: Dousova, H – volume: 64 start-page: 8067 year: 2008 ident: WOS:000258411600005 article-title: Rapid synthesis of the tetrahydroquinoline alkaloids: angustureine, cuspareine and galipinine publication-title: TETRAHEDRON doi: 10.1016/j.tet.2008.06.073 contributor: fullname: O'Byrne, A – volume: 72 start-page: 5244 year: 2007 ident: WOS:000247612200027 article-title: Wittig reactions in water media employing stabilized ylides with aldehydes. Synthesis of alpha,beta-unsaturated esters from mixing aldehydes, alpha-bromoesters, and Ph3P in aqueous NaHCO3 publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo070665k contributor: fullname: El-Batta, A – volume: 47 start-page: 179 year: 2015 ident: 000407524200025.1 publication-title: Org Prep Proced Int. contributor: fullname: Diaz-Munoz, G – volume: 133 start-page: 19006 year: 2011 ident: WOS:000297398900072 article-title: Iridium-Catalyzed Allylic Vinylation and Asymmetric Allylic Amination Reactions with o-Aminostyrenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja2092954 contributor: fullname: Ye, KY – volume: 64 start-page: 762 year: 1998 ident: WOS:000077915200021 article-title: Alkaloids from Galipea officinalis publication-title: PLANTA MEDICA contributor: fullname: Rakotoson, JH – volume: 72 start-page: 6577 year: 2007 ident: WOS:000248793400032 article-title: A route to 2-substituted tetrahydroquinolines via palladium-catalyzed intramolecular hydroamination of anilino-alkynes publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0708137 contributor: fullname: Patil, NT – volume: 2008 start-page: 4622 year: 2008 ident: WOS:000259944100013 article-title: Synthesis of alkaloids of Galipea officinalis by alkylation of an alpha-amino nitrile publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.200800512 contributor: fullname: Shahane, S – volume: 51 start-page: 1167 year: 1999 ident: WOS:000081820200040 article-title: Two tetrahydroquinoline alkaloids from Galipea officinalis publication-title: PHYTOCHEMISTRY contributor: fullname: Jacquemond-Collet, I – volume: 5 start-page: 38846 year: 2015 ident: WOS:000354201500006 article-title: An enantioselective approach to 2-alkyl substituted tetrahydroquinolines: total synthesis of (+)-angustureine publication-title: RSC ADVANCES doi: 10.1039/c5ra05987a contributor: fullname: Garg, Y – volume: 37 start-page: 3873 year: 1981 ident: WOS:A1981MT84600001 article-title: FURTHER SYNTHETIC STUDIES ON RIFAMYCIN-S publication-title: TETRAHEDRON contributor: fullname: NAGAOKA, H – volume: 14 start-page: 9868 year: 2008 ident: WOS:000261074800010 article-title: Organocatalytic Approach to Benzofused Nitrogen-Containing Heterocycles: Enantioselective Total Synthesis of (+)-Angustureine publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200801480 contributor: fullname: Fustero, S – volume: 125 start-page: 10536 year: 2003 ident: WOS:000185012800027 article-title: Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0353762 contributor: fullname: Wang, WB – volume: 68 start-page: 68 year: 2002 ident: WOS:000173857600015 article-title: Antiplasmodial and cytotoxic activity of galipinine and other tetrahydroquinolines from Galipea officinalis publication-title: PLANTA MEDICA contributor: fullname: Jacquemond-Collet, I – volume: 15 start-page: 869 year: 2011 ident: WOS:000288985500008 article-title: Syntheses of 2,3-Dihydro-1,4-Benzodioxins and Bioisosteres as Structural Motifs for Biologically Active Compounds publication-title: CURRENT ORGANIC CHEMISTRY contributor: fullname: Cruz-Lopez, O – volume: 73 start-page: 8030 year: 2008 ident: WOS:000259973900025 article-title: A three-step route to a tricyclic steroid precursor publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo801767n contributor: fullname: Taber, DF – volume: 54 start-page: 1312 year: 2013 ident: WOS:000315321600033 article-title: Synthesis of (-)-(R)-angustureine by formal alkynylation of a chiral beta-amino ester publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2012.12.122 contributor: fullname: Tummatorn, J – volume: 45 start-page: 2260 year: 2006 ident: WOS:000236506000020 article-title: Asymmetric hydrogenation of quinolines and isoquinolines activated by chloroformates publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200503073 contributor: fullname: Lu, SM – volume: 13 start-page: 2544 year: 2011 ident: WOS:000290465800009 article-title: Conjugate Addition of Lithium N-Phenyl-N-(alpha-methylbenzyl)amide: Application to the Asymmetric Synthesis of (R)-(-)-Angustureine publication-title: ORGANIC LETTERS doi: 10.1021/ol200625h contributor: fullname: Bentley, SA – volume: 59 start-page: 6785 year: 2003 ident: WOS:000184960000008 article-title: The aza-xylylene Diels-Alder approach for the synthesis of naturally occurring 2-alkyl tetrahydroquinolines publication-title: TETRAHEDRON doi: 10.1016/S0040-4020(03)00915-3 contributor: fullname: Avemaria, F – volume: 16 start-page: 827 year: 2005 ident: WOS:000227266700010 article-title: Total synthesis of (+)-(S)-angustureine and the determination of the absolute configuration of the natural product angustureine publication-title: TETRAHEDRON-ASYMMETRY doi: 10.1016/j.tetasy.2004.12.022 contributor: fullname: Theeraladanon, C – volume: 2011 start-page: 6877 year: 2011 ident: WOS:000297205800007 article-title: Enantioselective Syntheses of Tetrahydroquinolines Based on Iridium-Catalyzed Allylic Substitutions: Total Syntheses of (+)-Angustureine and (-)-Cuspareine publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201100981 contributor: fullname: Satyanarayana, G – volume: 128 start-page: 12656 year: 2006 ident: WOS:000240795000034 article-title: A concise total synthesis of DL-histrionicotoxin publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja065015x contributor: fullname: Karatholuvhu, MS – volume: 10 start-page: 4424 year: 2012 ident: WOS:000304097000015 article-title: Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c2ob25122a contributor: fullname: Taylor, LL – volume: 16 start-page: 827 year: 2005 ident: 10.1016/j.tetlet.2017.07.044_h0045 article-title: Nishida A publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2004.12.022 contributor: fullname: Theeraladanon – start-page: 4622 year: 2008 ident: 10.1016/j.tetlet.2017.07.044_h0075 publication-title: Eur J Org Chem doi: 10.1002/ejoc.200800512 contributor: fullname: Shahane – volume: 5 start-page: 38846 year: 2015 ident: 10.1016/j.tetlet.2017.07.044_h0140 publication-title: RSC Adv doi: 10.1039/C5RA05987A contributor: fullname: Garg – volume: 45 start-page: 3683 year: 2006 ident: 10.1016/j.tetlet.2017.07.044_h0055 publication-title: Angew Chem Int Ed doi: 10.1002/anie.200600191 contributor: fullname: Rueping – volume: 47 start-page: 179 year: 2015 ident: 10.1016/j.tetlet.2017.07.044_b0005 publication-title: Org Prep Proced Int doi: 10.1080/00304948.2015.1025012 contributor: fullname: Diaz-Muñoz – volume: 133 start-page: 19006 year: 2011 ident: 10.1016/j.tetlet.2017.07.044_h0120 publication-title: J Am Chem Soc doi: 10.1021/ja2092954 contributor: fullname: Ye – volume: 68 start-page: 68 year: 2002 ident: 10.1016/j.tetlet.2017.07.044_b0025 publication-title: Planta Med doi: 10.1055/s-2002-19869 contributor: fullname: Jacquemond-Collet – volume: 54 start-page: 1312 year: 2013 ident: 10.1016/j.tetlet.2017.07.044_h0130 publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2012.12.122 contributor: fullname: Tummatorn – volume: 37 start-page: 3873 year: 1981 ident: 10.1016/j.tetlet.2017.07.044_b0055 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)93261-2 contributor: fullname: Nagaoka – volume: 13 start-page: 2544 year: 2011 ident: 10.1016/j.tetlet.2017.07.044_h0105 publication-title: Org Lett doi: 10.1021/ol200625h contributor: fullname: Bentley – volume: 72 start-page: 5244 year: 2007 ident: 10.1016/j.tetlet.2017.07.044_h0150 publication-title: J Org Chem doi: 10.1021/jo070665k contributor: fullname: El-Batta – volume: 128 start-page: 12656 year: 2006 ident: 10.1016/j.tetlet.2017.07.044_b0050 publication-title: J Am Chem Soc doi: 10.1021/ja065015x contributor: fullname: Karatholuvhu – volume: 51 start-page: 1167 year: 1999 ident: 10.1016/j.tetlet.2017.07.044_b0010 publication-title: Phytochemistry doi: 10.1016/S0031-9422(99)00032-1 contributor: fullname: Jacquemond-Collet – volume: 72 start-page: 6577 year: 2007 ident: 10.1016/j.tetlet.2017.07.044_h0065 publication-title: J Org Chem doi: 10.1021/jo0708137 contributor: fullname: Patil – volume: 27 start-page: 631 year: 2006 ident: 10.1016/j.tetlet.2017.07.044_h0060 publication-title: Bull Korean Chem Soc doi: 10.5012/bkcs.2006.27.5.631 contributor: fullname: Ryu – volume: 125 start-page: 10536 year: 2003 ident: 10.1016/j.tetlet.2017.07.044_h0030 publication-title: J Am Chem Soc doi: 10.1021/ja0353762 contributor: fullname: Wang – volume: 64 start-page: 8067 year: 2008 ident: 10.1016/j.tetlet.2017.07.044_h0070 publication-title: Tetrahedron doi: 10.1016/j.tet.2008.06.073 contributor: fullname: O’Byrne – volume: 22 start-page: 932 year: 2004 ident: 10.1016/j.tetlet.2017.07.044_h0040 publication-title: Chin J Chem doi: 10.1002/cjoc.20040220911 contributor: fullname: Lin – volume: 10 start-page: 4424 year: 2012 ident: 10.1016/j.tetlet.2017.07.044_h0125 publication-title: Org Biomol Chem doi: 10.1039/c2ob25122a contributor: fullname: Taylor – volume: 36 start-page: 2939 year: 2006 ident: 10.1016/j.tetlet.2017.07.044_h0145 publication-title: Synth Commun doi: 10.1080/00397910600773684 contributor: fullname: Wu – volume: 73 start-page: 8030 year: 2008 ident: 10.1016/j.tetlet.2017.07.044_b0060 publication-title: J Org Chem doi: 10.1021/jo801767n contributor: fullname: Taber – volume: 15 start-page: 869 year: 2011 ident: 10.1016/j.tetlet.2017.07.044_h0100 publication-title: Curr Org Chem doi: 10.2174/138527211794518925 contributor: fullname: Cruz-Lopez – start-page: 6877 year: 2011 ident: 10.1016/j.tetlet.2017.07.044_h0115 publication-title: Eur J Org Chem doi: 10.1002/ejoc.201100981 contributor: fullname: Satyanarayana – volume: 44 start-page: 123 year: 1973 ident: 10.1016/j.tetlet.2017.07.044_b0020 publication-title: Fitoterapia contributor: fullname: Mester – volume: 64 start-page: 762 year: 1998 ident: 10.1016/j.tetlet.2017.07.044_b0015 publication-title: Planta Med doi: 10.1055/s-2006-957578 contributor: fullname: Rakotoson – volume: 11 start-page: 884 year: 2015 ident: 10.1016/j.tetlet.2017.07.044_h0135 publication-title: Beilstein J Org Chem doi: 10.3762/bjoc.11.99 contributor: fullname: Dousová – volume: 75 start-page: 941 year: 2010 ident: 10.1016/j.tetlet.2017.07.044_h0095 publication-title: J Org Chem doi: 10.1021/jo902424m contributor: fullname: Chen – volume: 580 start-page: 44 year: 1953 ident: 10.1016/j.tetlet.2017.07.044_b0040 publication-title: Liebigs Ann doi: 10.1002/jlac.19535800107 contributor: fullname: Wittig – volume: 133 start-page: 9878 year: 2011 ident: 10.1016/j.tetlet.2017.07.044_h0110 publication-title: J Am Chem Soc doi: 10.1021/ja2023042 contributor: fullname: Wang – volume: 11 start-page: 767 year: 2009 ident: 10.1016/j.tetlet.2017.07.044_h0085 publication-title: Green Chem doi: 10.1039/b822822a contributor: fullname: Wang – volume: 14 start-page: 9868 year: 2008 ident: 10.1016/j.tetlet.2017.07.044_h0080 publication-title: Chem Eur J doi: 10.1002/chem.200801480 contributor: fullname: Fustero – volume: 74 start-page: 5947 year: 2009 ident: 10.1016/j.tetlet.2017.07.044_h0090 publication-title: J Org Chem doi: 10.1021/jo900917q contributor: fullname: Kothandaraman – volume: 59 start-page: 6785 year: 2003 ident: 10.1016/j.tetlet.2017.07.044_h0035 publication-title: Tetrahedron doi: 10.1016/S0040-4020(03)00915-3 contributor: fullname: Avemaria – volume: 45 start-page: 2260 year: 2006 ident: 10.1016/j.tetlet.2017.07.044_h0050 publication-title: Angew Chem Int Ed doi: 10.1002/anie.200503073 contributor: fullname: Wang – volume: 92 start-page: 226 year: 1970 ident: 10.1016/j.tetlet.2017.07.044_b0045 publication-title: J Am Chem Soc doi: 10.1021/ja00704a052 contributor: fullname: Corey |
| SSID | ssj0000680 |
| Score | 2.3364055 |
| Snippet | [Display omitted]
•The total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids, was carry out in three steps and high yields.•The key step of this approach is... The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (+/-)-galipinine, (+/-)-cuspareine, (+/-)-galipeine and... |
| Source | Web of Science |
| SourceID | crossref webofscience elsevier |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 3311 |
| SubjectTerms | Chemistry Chemistry, Organic Galipea officinalis Phase transfer medium Physical Sciences Science & Technology Tetrahydroquinoline alkaloids Wittig reaction |
| Title | A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction |
| URI | https://dx.doi.org/10.1016/j.tetlet.2017.07.044 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000407524200025 |
| Volume | 58 |
| WOS | 000407524200025 |
| WOSCitedRecordID | wos000407524200025 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV07b9swECZSe2iXoukDdZMYHLyqlixSpEbDSOCmSKYY9Sbw6ao1JCNWBi9Ff3ruKKlwgBYtCmmRcIQoHnHfd-TdkZCJ90qnQqvISJlGTHMdSa9lpJibxV7EOg9Fkm5us-WKXa_5-oQs-lwYDKvsbH9r04O17t5Mu9Gc7soSc3wZXCn4G2ks8xj89iHAEe7VDuefPi9vjwyyjPvgOWzQZ9CFMK_GgU4wqDIRoYonY39CqN8AUwChq1fkZcce6bzt4Ck5cdVr8nzRH9r2hvycU3Bw8aQMqipLXSgQAbhC94cKqN6-3NPaU-gN2JiDRVQoKzy2B8S339W2Lu2eYij8hoI03X0FjKNN4LbunoYsE2Co9Avua2xovXW-bFcTKXDPkCHxlqyuLu8Wy6g7ZCEy4C00oJk41cxn1krhBXOMz-Islzrj3Fpg3o7pTBhgLVj5j2WGeQuongttrPAglr4jg6qu3HtCvUm4UjnXRlsmnFGezYyacSM1kDgnRiTqB7bYtbU0ij7I7FvRKqJARRQx3IyNiOhHv3gyJwow939pOTlW1q-vIYMFjgQ_gEjARyT5F7FFVy0dqwQ0H_67U2fkBT7hgnSSnZNBc__gLoDRNHpMnn38kYy7efsIo5v5JA |
| link.rule.ids | 314,780,784,4502,24116,27924,27925,45585,45679 |
| linkProvider | Elsevier |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lb9NAEF5V5RAuqFAQoRT2kKupHc9618coahVoklMierP2WQyRE9XmkEvVn87s2kZBAlFV9skey-ud1XzfrOdByMg5qVKuZKSFSCNQTEXCKRFJsOPY8VjloUjSYpnN1vDlht0ckWmfC-PDKjvb39r0YK27KxfdbF7sytLn-AIeKfobaSzyGP32Z8CQ_eKi_nSfHJhjEfehc168z58LQV6NRY34kMqEhxqeAP_Cp7_AUoCgqxPyouOOdNIO7yU5stUrMpj2LdtOycOEonvr-2RQWRlqQ3kIRBVa7yskenVZ062jOBq0MHvjMaGsfNMeFN_8kJttaWrqA-FvKUrT3TdEONoEZmvvaMgxQX5Kv_q_Grd0u7GubPcSKTLPkB_xmqyvLlfTWdS1WIg0-goN6iVOFbjMGMEdBwtsHGe5UBljxiDvtqAyrpGz-Lp_kGlwBjE950ob7lAsfUOOq21l3xLqdMKkzJnSygC3WjoYazlmWiikcJYPSdRPbLFrK2kUfYjZ96JVROEVUcR4AgwJ72e_-GNFFGjs__Pk6FBZv9_m-SsyJPwAjwNsSJLHiE27Wum-RkDz7smD-kgGs9ViXsw_L6_PyHN_x29NJ9l7ctzc_bTnyG0a9SGs3V_re_n9 |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=A+concise+and+efficient+synthesis+of+tetrahydroquinoline+alkaloids+using+the+phase+transfer+mediated+Wittig+olefination+reaction&rft.jtitle=Tetrahedron+letters&rft.au=Diaz-Mu%C3%B1oz%2C+Gaspar&rft.au=Isidorio%2C+Raquel+Geralda&rft.au=Miranda%2C+Izabel+Luzia&rft.au=de+Souza+Dias%2C+Gabriel+Nunes&rft.date=2017-08-16&rft.pub=Elsevier+Ltd&rft.issn=0040-4039&rft.eissn=1873-3581&rft.volume=58&rft.issue=33&rft.spage=3311&rft.epage=3315&rft_id=info:doi/10.1016%2Fj.tetlet.2017.07.044&rft.externalDocID=S0040403917308900 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0040-4039&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0040-4039&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0040-4039&client=summon |