Asymmetric Total Synthesis and Formal Total Synthesis of the Antitumor Sesquiterpenoid (+)-Eremantholide A
A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda−Grubbs ring-closing metathesis (RCM) reaction is used to assemble the nine-membered oxonin ring, and an enolate alkylation between the 3(2H)-furanone 2 and O-triflate 3 is exploited for C(9)−C(10) bond constructio...
Saved in:
| Published in | Organic letters Vol. 9; no. 7; pp. 1267 - 1270 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
29.03.2007
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda−Grubbs ring-closing metathesis (RCM) reaction is used to assemble the nine-membered oxonin ring, and an enolate alkylation between the 3(2H)-furanone 2 and O-triflate 3 is exploited for C(9)−C(10) bond construction. An Evans asymmetric aldol reaction and a Sharpless asymmetric epoxidation served to stereoselectively install the C(6), C(7), and C(8) stereocenters of the target structure. |
|---|---|
| AbstractList | [structure: see text]. A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda-Grubbs ring-closing metathesis (RCM) reaction is used to assemble the nine-membered oxonin ring, and an enolate alkylation between the 3(2H)-furanone 2 and O-triflate 3 is exploited for C(9)-C(10) bond construction. An Evans asymmetric aldol reaction and a Sharpless asymmetric epoxidation served to stereoselectively install the C(6), C(7), and C(8) stereocenters of the target structure. A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda-Grubbs ring-closing metathesis (RCM) reaction is used to assemble the nine-membered oxonin ring, and an enolate alkylation between the 3(2H)-furanone 2 and O-triflate 3 is exploited for C(9)-C(10) bond construction. An Evans asymmetric aldol reaction and a Sharpless asymmetric epoxidation served to stereoselectively install the C(6), C(7), and C(8) stereocenters of the target structure. A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda−Grubbs ring-closing metathesis (RCM) reaction is used to assemble the nine-membered oxonin ring, and an enolate alkylation between the 3(2H)-furanone 2 and O-triflate 3 is exploited for C(9)−C(10) bond construction. An Evans asymmetric aldol reaction and a Sharpless asymmetric epoxidation served to stereoselectively install the C(6), C(7), and C(8) stereocenters of the target structure. |
| Author | Hale, Karl J Li, Yi |
| Author_xml | – sequence: 1 givenname: Yi surname: Li fullname: Li, Yi – sequence: 2 givenname: Karl J surname: Hale fullname: Hale, Karl J |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/17326647$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkEFrGzEQhUVJaOK0h_6BspeGBrPpSNqV5KMxSRMw5JD0vGi1s1RmV3IkLcH_PkptXCg95DLzmPneMLwZOXHeISFfKFxTYPSHH0ACKME-kHNaM15KqNnJUQs4I7MYNwA0TxYfyRmVnAlRyXOyWcbdOGIK1hRPPumheNy59BujjYV2XXHrw5iH_658X2RVLF2yaRp9KB4xPk82Ydii87Yrvs-vypuAo84OP9gus5_Iaa-HiJ8P_YL8ur15Wt2V64ef96vlutRcLlIpNFUt7biqRA9VL6iRmhnotGhRcSWRi5YD0l4aoQwzrEZTozatyUUtKL8gl_u72-CfJ4ypGW00OAzaoZ9iI4FTqiqZwas9aIKPMWDfbIMdddg1FJq3YJtjsJn9ejg6tSN2f8lDkhmY74EXbH0fjUVn8IgBAKtqUBX_ozKt3k-vbNLJerfyk0vZ-m1v1SY2Gz8Fl8P8z8evlxiiVA |
| CitedBy_id | crossref_primary_10_1039_c1ob05567d crossref_primary_10_1002_ange_201400932 crossref_primary_10_1016_j_tet_2018_08_045 crossref_primary_10_1016_j_molstruc_2021_131004 crossref_primary_10_1016_j_tetlet_2008_04_071 crossref_primary_10_1021_ol200741j crossref_primary_10_1039_C9OB01096C crossref_primary_10_1016_j_tet_2017_01_017 crossref_primary_10_1021_jo070862j crossref_primary_10_1021_acs_joc_6b02838 crossref_primary_10_1016_j_tetasy_2017_06_002 crossref_primary_10_1021_acs_joc_7b00399 crossref_primary_10_1039_C7RA07317H crossref_primary_10_1002_ange_202402050 crossref_primary_10_1002_anie_202108336 crossref_primary_10_1021_jo102416e crossref_primary_10_1002_ange_201510709 crossref_primary_10_1002_tcr_201700104 crossref_primary_10_1021_acs_joc_2c02790 crossref_primary_10_1021_acs_joc_4c00090 crossref_primary_10_1134_S0022476619060131 crossref_primary_10_1021_ol9008365 crossref_primary_10_1021_ol203183k crossref_primary_10_1007_s41666_018_0020_2 crossref_primary_10_1016_j_ccr_2008_12_013 crossref_primary_10_1002_anie_202402050 crossref_primary_10_1021_acs_orglett_0c02505 crossref_primary_10_1002_slct_202002188 crossref_primary_10_1016_j_tet_2013_03_007 crossref_primary_10_1016_j_tetlet_2017_11_035 crossref_primary_10_1021_ol301090v crossref_primary_10_1039_c1ob05734k crossref_primary_10_1021_ol202241r crossref_primary_10_1016_j_electacta_2008_09_057 crossref_primary_10_1002_ejoc_202300573 crossref_primary_10_1021_acs_joc_5b00356 crossref_primary_10_1039_C8QO01132J crossref_primary_10_1002_anie_201109080 crossref_primary_10_1021_acs_joc_9b00076 crossref_primary_10_1021_acs_orglett_2c01845 crossref_primary_10_1002_ajoc_202200410 crossref_primary_10_1021_cr3003455 crossref_primary_10_1021_acs_joc_6b01528 crossref_primary_10_1002_ajoc_202000401 crossref_primary_10_1016_j_tet_2013_05_125 crossref_primary_10_1016_j_tetlet_2013_09_056 crossref_primary_10_1134_S107042801411013X crossref_primary_10_1016_j_tetlet_2012_01_053 crossref_primary_10_1002_anie_201812140 crossref_primary_10_1002_chin_200732193 crossref_primary_10_1021_acs_joc_1c00423 crossref_primary_10_1021_acs_joc_5b01076 crossref_primary_10_1089_aid_2014_0199 crossref_primary_10_1039_c1cc15319f crossref_primary_10_1002_anie_201400932 crossref_primary_10_1021_acs_joc_8b02153 crossref_primary_10_1016_j_tetlet_2013_10_150 crossref_primary_10_1080_00397911_2020_1821226 crossref_primary_10_1021_ol1011532 crossref_primary_10_1039_D3QO00558E crossref_primary_10_1016_j_tetlet_2015_09_124 crossref_primary_10_1002_adsc_201801382 crossref_primary_10_1021_cr800332c crossref_primary_10_1002_ange_201812140 crossref_primary_10_1021_jo100048j crossref_primary_10_1002_ejoc_202001005 crossref_primary_10_1039_C9OB02166C crossref_primary_10_1080_00397910903534023 crossref_primary_10_1002_ejoc_201900174 crossref_primary_10_1002_ange_202108336 crossref_primary_10_1021_ol901081a crossref_primary_10_1002_ange_201109080 crossref_primary_10_1038_s41467_019_13175_5 crossref_primary_10_1016_j_tet_2015_02_074 crossref_primary_10_1002_anie_201510709 |
| Cites_doi | 10.1021/ja044123l 10.1016/S0040-4020(03)00776-2 10.1021/ol016800b 10.1021/ol005850y 10.1039/c39900000843 10.1021/ja00025a049 10.1021/ja00217a039 10.1021/ja00398a058 10.1016/S0957-4166(02)00334-8 10.1016/S0040-4020(01)85435-1 10.1021/ja983222u 10.1016/S0040-4020(97)10427-6 10.1021/jo971046m 10.1021/jo01292a055 10.1039/p19800002866 10.1021/ja00856a059 10.1021/ja00253a032 10.1016/S0040-4039(02)02489-9 10.1055/s-1994-25538 10.1016/S0968-0896(99)00195-9 |
| ContentType | Journal Article |
| Copyright | Copyright © 2007 American Chemical Society |
| Copyright_xml | – notice: Copyright © 2007 American Chemical Society |
| DBID | 1KM 1KN BLEPL DTL GAMXJ CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 |
| DOI | 10.1021/ol0700862 |
| DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2007 Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef MEDLINE - Academic |
| DatabaseTitle | Web of Science MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef MEDLINE - Academic |
| DatabaseTitleList | MEDLINE Web of Science MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 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 | 1523-7052 |
| EndPage | 1270 |
| ExternalDocumentID | 10_1021_ol0700862 17326647 000245084300024 b726787008 |
| Genre | Research Support, Non-U.S. Gov't Journal Article |
| GrantInformation_xml | – fundername: Engineering and Physical Sciences Research Council; UK Research & Innovation (UKRI); Engineering & Physical Sciences Research Council (EPSRC) grantid: GR/S81582/01 |
| GroupedDBID | - .K2 123 4.4 53G 55A 5VS 7~N AABXI ABFLS ABMVS ABPTK ABUCX ACGFS ACS AEESW AENEX AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH CS3 DU5 DZ EBS ED ED~ F5P GNL IH9 IHE JG JG~ K2 LG6 P2P RNS ROL TN5 UI2 UNC VF5 VG9 W1F X YNT --- -DZ -~X 1KM 1KN AAHBH ABJNI ABQRX ADHLV AHGAQ BLEPL CUPRZ DTL GGK GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 |
| ID | FETCH-LOGICAL-a379t-6a18b1d3846f04f61c7a2c0da6be8387e36b30e1f7c68c2c25ec5eacbceac8913 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 84 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000245084300024 |
| ISSN | 1523-7060 |
| IngestDate | Fri Aug 16 08:08:52 EDT 2024 Fri Aug 23 00:59:31 EDT 2024 Sat Sep 28 07:56:43 EDT 2024 Fri Nov 08 20:04:02 EST 2024 Tue Sep 17 23:55:53 EDT 2024 Thu Aug 27 13:43:00 EDT 2020 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 7 |
| Keywords | OXIDATION ALCOHOLS DEPROTONATION ENANTIOSELECTIVE SYNTHESIS LACTONES METATHESIS |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a379t-6a18b1d3846f04f61c7a2c0da6be8387e36b30e1f7c68c2c25ec5eacbceac8913 |
| Notes | researchfish ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| PMID | 17326647 |
| PQID | 70311847 |
| PQPubID | 23479 |
| PageCount | 4 |
| ParticipantIDs | acs_journals_10_1021_ol0700862 webofscience_primary_000245084300024 pubmed_primary_17326647 webofscience_primary_000245084300024CitationCount proquest_miscellaneous_70311847 crossref_primary_10_1021_ol0700862 |
| ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 |
| PublicationCentury | 2000 |
| PublicationDate | 2007-03-29 |
| PublicationDateYYYYMMDD | 2007-03-29 |
| PublicationDate_xml | – month: 03 year: 2007 text: 2007-03-29 day: 29 |
| PublicationDecade | 2000 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Organic letters |
| PublicationTitleAbbrev | ORG LETT |
| PublicationTitleAlternate | Org. Lett |
| PublicationYear | 2007 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | Nickel, A (WOS:000225808200013) 2004; 126 LEQUESNE, PW (WOS:A1978GD27600023) 1978 MARSHALL, JA (WOS:A1988N319800039) 1988; 110 GAREGG, PJ (WOS:A1980KV25200043) 1980 Kingsbury, JS (WOS:000078471800024) 1999; 121 Chimichi, S (WOS:000184017700007) 2003; 59 BOECKMAN, RK (WOS:A1991GT65500049) 1991; 113 Hansen, TM (WOS:000180094700012) 2003; 44 GAO, Y (WOS:A1987K110600032) 1987; 109 HLADON, B (WOS:A1979HE04300005) 1979; 31 Takao, K (WOS:A1995TK91900017) 1995; 60 DeMico, A (WOS:A1997XZ71900043) 1997; 62 Grubbs, RH (WOS:000073062600001) 1998; 54 EVANS, DA (WOS:A1981LM32700057) 1981; 103 Hale, KJ (WOS:000088346400003) 2000; 2 YADAV, JS (WOS:A1990DK06400031) 1990 Hale, KJ (WOS:000172181700048) 2001; 3 WHITESELL, JK (WOS:A1980JF34300055) 1980; 45 Shi, HX (WOS:000177467900014) 2002; 13 CAIN, CM (WOS:A1990CL16300022) 1990; 46 LEY, SV (WOS:A1994NX33700001) 1994 Rungeler, P (WOS:000084153100009) 1999; 7 RAFFAUF, RF (WOS:A1975AW22500059) 1975; 97 Ley S. V. (ol0700862b00011/ol0700862b00011_1) 1994 Cain C. M. (ol0700862b00006/ol0700862b00006_3) 1990; 46 De Mico A. (ol0700862b00012/ol0700862b00012_1) 1997; 62 Important Note (ol0700862b00017/ol0700862b00017_1) Hale K. J. (ol0700862b00010/ol0700862b00010_1) 2000; 2 ol0700862b00015/ol0700862b00015_1 Garegg P. J. (ol0700862b00013/ol0700862b00013_1) 1980 (ol0700862b00002/ol0700862b00002_1) 1991; 113 (ol0700862b00018/ol0700862b00018_3) 2004; 126 Chimichi S. (ol0700862b00005/ol0700862b00005_1) 2003; 59 Marshall J. A. (ol0700862b00006/ol0700862b00006_2) 1988; 110 Hladon B. (ol0700862b00003/ol0700862b00003_1) 1979; 31 Hale K. J. (ol0700862b00009/ol0700862b00009_1) 2001; 3 Yadav J. S. (ol0700862b00014/ol0700862b00014_1) 1990 Gao Y. (ol0700862b00007/ol0700862b00007_1) 1987; 109 Although (ol0700862b00004/ol0700862b00004_1) 1999; 7 Whitesell J. K. (ol0700862b00006/ol0700862b00006_1) 1980; 45 Evans D. A. (ol0700862b00008/ol0700862b00008_1) 1981; 103 Hansen T. M. (ol0700862b00016/ol0700862b00016_1) 2003; 44 Grubbs R. H. (ol0700862b00018/ol0700862b00018_2) 1998; 54 Kingsbury J. S. (ol0700862b00018/ol0700862b00018_1) 1999; 121 Eremantholide (ol0700862b00001/ol0700862b00001_1) 1975; 97 |
| References_xml | – volume: 126 start-page: 16300 year: 2004 ident: WOS:000225808200013 article-title: Total synthesis of ingenol publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja044123l contributor: fullname: Nickel, A – volume: 59 start-page: 5215 year: 2003 ident: WOS:000184017700007 article-title: New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity publication-title: TETRAHEDRON doi: 10.1016/S0040-4020(03)00776-2 contributor: fullname: Chimichi, S – volume: 113 start-page: 9682 year: 1991 ident: WOS:A1991GT65500049 article-title: SYNTHETIC STUDIES DIRECTED TOWARD THE EREMANTHOLIDES .2. A NOVEL APPLICATION OF THE RAMBERG-BACKLUND REARRANGEMENT TO A HIGHLY STEREOSELECTIVE SYNTHESIS OF (+)-EREMANTHOLIDE-A publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: BOECKMAN, RK – volume: 121 start-page: 791 year: 1999 ident: WOS:000078471800024 article-title: A recyclable Ru-based metathesis catalyst publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Kingsbury, JS – volume: 13 start-page: 1423 year: 2002 ident: WOS:000177467900014 article-title: Enantioselective synthesis of the PAF antagonist MK-287 publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Shi, HX – volume: 62 start-page: 6974 year: 1997 ident: WOS:A1997XZ71900043 article-title: A versatile and highly selective hypervalent iodine (III)/2,2,6,6-tetramethyl-1-piperidinyloxyl-mediated oxidation of alcohols to carbonyl compounds publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: DeMico, A – volume: 7 start-page: 2343 year: 1999 ident: WOS:000084153100009 article-title: Inhibition of transcription factor NF-kappa B by sesquiterpene lactones: a proposed molecular mechanism of action publication-title: BIOORGANIC & MEDICINAL CHEMISTRY contributor: fullname: Rungeler, P – volume: 3 start-page: 3791 year: 2001 ident: WOS:000172181700048 article-title: A short synthetic pathway to a fully-functionalized southern hemisphere of the antitumor macrolide bryostatin 1 publication-title: ORGANIC LETTERS doi: 10.1021/ol016800b contributor: fullname: Hale, KJ – start-page: 1572 year: 1978 ident: WOS:A1978GD27600023 article-title: ANTITUMOUR PLANTS .6. NOVEL MODIFIED GERMACRANOLIDES AND OTHER CONSTITUENTS OF EREMANTHUS-ELAEAGNUS SCHULTZ-BIP (COMPOSITAE) publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: LEQUESNE, PW – volume: 54 start-page: 4413 year: 1998 ident: WOS:000073062600001 article-title: Recent advances in olefin metathesis and its application in organic synthesis publication-title: TETRAHEDRON contributor: fullname: Grubbs, RH – volume: 109 start-page: 5765 year: 1987 ident: WOS:A1987K110600032 article-title: CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: GAO, Y – volume: 110 start-page: 2925 year: 1988 ident: WOS:A1988N319800039 article-title: ENANTIOSELECTIVE SYNTHESIS OF MACROCYCLIC PROPARGYLIC ALCOHOLS BY [2,3] WITTIG RING CONTRACTION - SYNTHESIS OF (+)-ARISTOLACTONE AND CEMBRANOID PRECURSORS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MARSHALL, JA – volume: 60 start-page: 8179 year: 1995 ident: WOS:A1995TK91900017 article-title: Novel total synthesis of (+)-eremantholide A publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Takao, K – volume: 44 start-page: 57 year: 2003 ident: WOS:000180094700012 article-title: Highly chemoselective oxidation of 1,5-diols to delta-lactones with TEMPO/BAIB publication-title: TETRAHEDRON LETTERS contributor: fullname: Hansen, TM – volume: 45 start-page: 755 year: 1980 ident: WOS:A1980JF34300055 article-title: ASYMMETRIC INDUCTION .3. ENANTIOSELECTIVE DEPROTONATION BY CHIRAL LITHIUM AMIDE BASES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: WHITESELL, JK – start-page: 2866 year: 1980 ident: WOS:A1980KV25200043 article-title: NOVEL REAGENT SYSTEM FOR CONVERTING A HYDROXY-GROUP INTO AN IODO-GROUP IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION .2. publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: GAREGG, PJ – start-page: 843 year: 1990 ident: WOS:A1990DK06400031 article-title: TITANOCENE INDUCED REGIOSELECTIVE DEOXYGENATION OF 2,3-EPOXY ALCOHOLS - A NEW REACTION FOR THE SYNTHESIS OF ALLYLIC ALCOHOLS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: YADAV, JS – volume: 46 start-page: 523 year: 1990 ident: WOS:A1990CL16300022 article-title: ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES publication-title: TETRAHEDRON contributor: fullname: CAIN, CM – volume: 31 start-page: 35 year: 1979 ident: WOS:A1979HE04300005 article-title: SESQUITERPENE LACTONES .25. STUDIES ON THE MODE OF ACTION - CELLULAR AND MOLECULAR-BASIS OF CYTOSTATIC ACTION publication-title: POLISH JOURNAL OF PHARMACOLOGY AND PHARMACY contributor: fullname: HLADON, B – volume: 2 start-page: 2189 year: 2000 ident: WOS:000088346400003 article-title: Control of olefin geometry in the bryostatin B-ring through exploitation of a C(2)-symmetry breaking tactic and a Smith-Tietze coupling reaction publication-title: ORGANIC LETTERS doi: 10.1021/ol005850y contributor: fullname: Hale, KJ – volume: 97 start-page: 6884 year: 1975 ident: WOS:A1975AW22500059 article-title: EREMANTHOLIDE-A, A NOVEL TUMOR-INHIBITING COMPOUND FROM ERAMANTHUS-ELAEAGNUS SCHULTZ-BIP (COMPOSITAE) publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: RAFFAUF, RF – start-page: 639 year: 1994 ident: WOS:A1994NX33700001 article-title: TETRAPROPYLAMMONIUM PERRUTHENATE, PR4N+RUO4-, TPAP - A CATALYTIC OXIDANT FOR ORGANIC-SYNTHESIS publication-title: SYNTHESIS-STUTTGART contributor: fullname: LEY, SV – volume: 103 start-page: 2127 year: 1981 ident: WOS:A1981LM32700057 article-title: ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: EVANS, DA – start-page: 843 year: 1990 ident: ol0700862b00014/ol0700862b00014_1 publication-title: Chem. Commun. doi: 10.1039/c39900000843 contributor: fullname: Yadav J. S. – volume: 113 start-page: 9682 year: 1991 ident: ol0700862b00002/ol0700862b00002_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00025a049 – volume: 110 start-page: 2925 year: 1988 ident: ol0700862b00006/ol0700862b00006_2 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00217a039 contributor: fullname: Marshall J. A. – volume: 103 start-page: 2127 year: 1981 ident: ol0700862b00008/ol0700862b00008_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00398a058 contributor: fullname: Evans D. A. – ident: ol0700862b00015/ol0700862b00015_1 doi: 10.1016/S0957-4166(02)00334-8 – volume: 46 start-page: 523 year: 1990 ident: ol0700862b00006/ol0700862b00006_3 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)85435-1 contributor: fullname: Cain C. M. – volume: 121 start-page: 791 year: 1999 ident: ol0700862b00018/ol0700862b00018_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja983222u contributor: fullname: Kingsbury J. S. – volume: 54 start-page: 4413 year: 1998 ident: ol0700862b00018/ol0700862b00018_2 publication-title: Tetrahedron doi: 10.1016/S0040-4020(97)10427-6 contributor: fullname: Grubbs R. H. – volume: 62 start-page: 6974 year: 1997 ident: ol0700862b00012/ol0700862b00012_1 publication-title: J. Org. Chem. doi: 10.1021/jo971046m contributor: fullname: De Mico A. – volume-title: we find that 27 is always formed alongside approximately 14−17% of a lactone migration product that is difficult to remove at this stage ident: ol0700862b00017/ol0700862b00017_1 contributor: fullname: Important Note – volume: 45 start-page: 755 year: 1980 ident: ol0700862b00006/ol0700862b00006_1 publication-title: J. Org. Chem. doi: 10.1021/jo01292a055 contributor: fullname: Whitesell J. K. – start-page: 2866 year: 1980 ident: ol0700862b00013/ol0700862b00013_1 publication-title: J. Chem. Soc., Perkin Trans. 1 doi: 10.1039/p19800002866 contributor: fullname: Garegg P. J. – volume: 126 start-page: 16300 year: 2004 ident: ol0700862b00018/ol0700862b00018_3 publication-title: J. L. J. Am. Chem. Soc. doi: 10.1021/ja044123l – volume: 97 start-page: 6884 year: 1975 ident: ol0700862b00001/ol0700862b00001_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00856a059 contributor: fullname: Eremantholide – volume: 3 start-page: 3791 year: 2001 ident: ol0700862b00009/ol0700862b00009_1 publication-title: Org. Lett. doi: 10.1021/ol016800b contributor: fullname: Hale K. J. – volume: 109 start-page: 5765 year: 1987 ident: ol0700862b00007/ol0700862b00007_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00253a032 contributor: fullname: Gao Y. – volume: 44 start-page: 57 year: 2003 ident: ol0700862b00016/ol0700862b00016_1 publication-title: J. Tetrahedron Lett. doi: 10.1016/S0040-4039(02)02489-9 contributor: fullname: Hansen T. M. – start-page: 639 year: 1994 ident: ol0700862b00011/ol0700862b00011_1 publication-title: Synthesis doi: 10.1055/s-1994-25538 contributor: fullname: Ley S. V. – volume: 2 start-page: 2198 year: 2000 ident: ol0700862b00010/ol0700862b00010_1 publication-title: Org. Lett. contributor: fullname: Hale K. J. – volume: 59 start-page: 5215 year: 2003 ident: ol0700862b00005/ol0700862b00005_1 publication-title: Tetrahedron doi: 10.1016/S0040-4020(03)00776-2 contributor: fullname: Chimichi S. – volume: 31 start-page: 35 year: 1979 ident: ol0700862b00003/ol0700862b00003_1 publication-title: Pol. J. Pharmacol. Pharm. contributor: fullname: Hladon B. – volume: 7 start-page: 2343 year: 1999 ident: ol0700862b00004/ol0700862b00004_1 publication-title: J. Bioorg. Med. Chem. doi: 10.1016/S0968-0896(99)00195-9 contributor: fullname: Although |
| SSID | ssj0011529 |
| Score | 2.233774 |
| Snippet | A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda−Grubbs ring-closing metathesis (RCM) reaction is used to assemble the... A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda-Grubbs ring-closing metathesis (RCM) reaction is used to assemble the... [structure: see text]. A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda-Grubbs ring-closing metathesis (RCM) reaction is... |
| Source | Web of Science |
| SourceID | proquest crossref pubmed webofscience acs |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 1267 |
| SubjectTerms | Alkylation Antineoplastic Agents, Phytogenic - chemical synthesis Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Chemistry Chemistry, Organic Cyclization Humans Molecular Structure Oxidation-Reduction Physical Sciences Science & Technology Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Stereoisomerism |
| Title | Asymmetric Total Synthesis and Formal Total Synthesis of the Antitumor Sesquiterpenoid (+)-Eremantholide A |
| URI | http://dx.doi.org/10.1021/ol0700862 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000245084300024 https://www.ncbi.nlm.nih.gov/pubmed/17326647 https://search.proquest.com/docview/70311847 |
| Volume | 9 |
| WOS | 000245084300024 |
| WOSCitedRecordID | wos000245084300024 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3fb9MwED6N7QFeGL_pBsOCPYCQR2K7TvJYlVUTErx0k_YWOc5ZKrTJaJKH8dfvnDRlqGPbS2TpLpHsO_u-5HLfARySy6pE5Rk3qBVXqCQ3QjjucgruLtFojS9O_v5Dn5ypb-fD8y348J8Mvgi_lHPySg-8H8COiGhTePwznq5TBRSAkpYUVUjuqWB6-qDrt_rQY6t_Q88Gnrwx9LRhZrILX_tine7vkl9HTZ0d2T-b3I23zeAJPF7BTDbq_OIpbGHxDB6O--5uz-HnqLpcLHw7LctOS0LgbHpZEBisZhUzRc4mHsvON0SlYzRiI1_c2yzKJZti9bvxZcwXWJSznH38_IkfL3FhPCnBfJaT7gs4mxyfjk_4qu8CNzJKaq5NGGdhLgmauEA5HdrICBvkRmcYyzhCqTMZYOgiq2MrrBiiHdIBnlm6-LTnS9guygJfA6PDM7BoExc7oZyJTaxRmWEgEpSZCMQADsgw6WrfVGmbEhdhul6yAbzvbZZedPwbNym9662Z0jL6lIcpsGyq1LPz0ztsNIBXnZH_PiQi4Kq95PC61dfyoE1KB7GS7WgA4X3UxitidU8oUO_dNbl9eNR9Kvbt9N7Adr1s8C1hnDo7aH38CsL99K8 |
| link.rule.ids | 315,783,787,2772,27088,27936,27937,57066,57116 |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1BT9swFLYYHNhlG7CxbgMsxIFpMktsx0mOVUVVNuDSInGLHMeWOtqE1cmB_fo9O2mBgTQukSW_WLbfi9-XvLzvIXQEJstTXuREasEJ15wRSakhpgDnblKhlXTJyReXYnTFf1xH1x1NjsuFgUlYGMn6IP49u0D4vZqBcTr8_QptRDE4SgeDBuNVxAD8UOq5USkjjhFmySL08FbngZR97IGewMpnPZD3NsO3bdkiP0__k8nNSVPnJ-rPPxSOL1vIO_SmA52431rJFlrT5TbaHCxrve2gX317N5-74loKTyrA43h8VwI0tFOLZVngoUO2syddlcHQwn2X6tvMqwUea_u7cUnNt7qspgU-_vaVnC70XDqKgtm0ANn36Gp4OhmMSFeFgUgWpzURMkzysGAAVEzAjQhVLKkKCilynbAk1kzkLNChiZVIFFU00iqC4zxXcHFB0A9ovaxK_RFhOEoDpVVqEkO5kYlMhOYyCmiqWU4D2kP7sGNZ9xTZzAfIaZittqyHDpeqy25bNo7nhA6WSs1gG10ARJa6amzmuPrhjTbuod1W1_eDxABjhes5eqj8VX_gQ9RBwplv9VD4ErFBR7Pu6AXqT_9b3AHaHE0uzrPzs8ufn9Hr9iOyK7T3Ba3Xi0bvAfqp831v9n8BqfT9FA |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Lb9QwEB5BkaAX3o_l0VqoBxBySWzHSY6rpavyKkjbSr1FjmNLS3eTZZ0cyq9n7M0uhVail8iSJ5YfY8_nTOYbgD1UWZGLqqTKSEGFEZwqxiy1FRp3m0ujlQ9O_nokD0_Ep9PktL8o-lgY7ITDllxw4vtdvahszzAQv29mqKAeg9-EW0kaB7fscDTZeA3QFuWBH5Vx6llh1kxCF1_1Vki7v63QJWh5pRUKFmd8D75t-hp-NDnb79pyX__6h8bx-oO5D3d78EmGK215ADdM_RDujNY53x7Bj6E7n899ki1NjhvE5WRyXiNEdFNHVF2RsUe4s0tVjSVYIkMf8tvNmyWZGPez88HNC1M304q8efeWHizNXHmqgtm0QtnHcDI-OB4d0j4bA1U8zVsqVZyVccURsNhIWBnrVDEdVUqWJuNZargseWRim2qZaaZZYnSCx3qp8eGdoU9gq25q8wwIHqmRNjq3mWXCqkxl0giVRCw3vGQRG8AOzlrR7yZXBEc5i4vNlA3g9Xr5isWKleMqod31whY4jd4RomrTdK7wnP14s00H8HS13n8aSRHOSl-zd1EBNvVRcFVHmeChNID4OmKjnm7d0wy0z_83uF24_f3DuPjy8ejzC9hefUv2-fZewla77MwrBEFtuRM0_zfXy_-O |
| 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=Asymmetric+total+synthesis+and+formal+total+synthesis+of+the+antitumor+sesquiterpenoid+%28%2B%29-eremantholide+A&rft.jtitle=Organic+letters&rft.au=Li%2C+Yi&rft.au=Hale%2C+Karl+J.&rft.date=2007-03-29&rft.pub=Amer+Chemical+Soc&rft.issn=1523-7060&rft.eissn=1523-7052&rft.volume=9&rft.issue=7&rft.spage=1267&rft.epage=1270&rft_id=info:doi/10.1021%2Fol0700862&rft_id=info%3Apmid%2F17326647&rft.externalDBID=n%2Fa&rft.externalDocID=000245084300024 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1523-7060&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1523-7060&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1523-7060&client=summon |