Total Synthesis of the Sesquiterpene (−)-Merrillianin
The first total synthesis of (−)-merrillianin (1), which is a natural sesquiterpene with a tricyclic structure having a cyclopentane ring and five- and seven-membered lactone parts, is demonstrated. This asymmetric total synthesis enabled the absolute stereostructure determination of naturally occur...
Saved in:
Published in | Organic letters Vol. 26; no. 16; pp. 3327 - 3331 |
---|---|
Main Authors | , , , , , , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
26.04.2024
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | The first total synthesis of (−)-merrillianin (1), which is a natural sesquiterpene with a tricyclic structure having a cyclopentane ring and five- and seven-membered lactone parts, is demonstrated. This asymmetric total synthesis enabled the absolute stereostructure determination of naturally occurring (−)-1. |
---|---|
AbstractList | The first total synthesis of (-)-merrillianin (1), which is a natural sesquiterpene with a tricyclic structure having a cyclopentane ring and five- and seven-membered lactone parts, is demonstrated. This asymmetric total synthesis enabled the absolute stereostructure determination of naturally occurring (-)-1. The first total synthesis of (−)-merrillianin (1), which is a natural sesquiterpene with a tricyclic structure having a cyclopentane ring and five- and seven-membered lactone parts, is demonstrated. This asymmetric total synthesis enabled the absolute stereostructure determination of naturally occurring (−)-1. The first total synthesis of (-)-merrillianin ( ), which is a natural sesquiterpene with a tricyclic structure having a cyclopentane ring and five- and seven-membered lactone parts, is demonstrated. This asymmetric total synthesis enabled the absolute stereostructure determination of naturally occurring (-)- . |
Author | Ogawa, Go Murata, Takatsugu Yonekura, Keita Toyoyama, Kiyotaka Sugimoto, Masuhiro Shimazaki, Takahisa Yamada, Tetsuro Iizumi, Takashi Taniguchi, Saori Shiina, Isamu Tateyama, Satoru Mori, Takahiro Yamai, Yu-suke Shinohara, Shojiro Suwa, Yuki Kageyama, Yosuke Ito, Keiichi Kuboki, Teppei |
AuthorAffiliation | Department of Applied Chemistry, Faculty of Science |
AuthorAffiliation_xml | – name: Department of Applied Chemistry, Faculty of Science |
Author_xml | – sequence: 1 givenname: Isamu orcidid: 0000-0002-8749-2540 surname: Shiina fullname: Shiina, Isamu email: shiina@rs.kagu.tus.ac.jp – sequence: 2 givenname: Takashi surname: Iizumi fullname: Iizumi, Takashi – sequence: 3 givenname: Saori surname: Taniguchi fullname: Taniguchi, Saori – sequence: 4 givenname: Masuhiro surname: Sugimoto fullname: Sugimoto, Masuhiro – sequence: 5 givenname: Takahisa surname: Shimazaki fullname: Shimazaki, Takahisa – sequence: 6 givenname: Yu-suke surname: Yamai fullname: Yamai, Yu-suke – sequence: 7 givenname: Go surname: Ogawa fullname: Ogawa, Go – sequence: 8 givenname: Tetsuro surname: Yamada fullname: Yamada, Tetsuro – sequence: 9 givenname: Shojiro surname: Shinohara fullname: Shinohara, Shojiro – sequence: 10 givenname: Yosuke surname: Kageyama fullname: Kageyama, Yosuke – sequence: 11 givenname: Teppei surname: Kuboki fullname: Kuboki, Teppei – sequence: 12 givenname: Yuki surname: Suwa fullname: Suwa, Yuki – sequence: 13 givenname: Keita surname: Yonekura fullname: Yonekura, Keita – sequence: 14 givenname: Keiichi surname: Ito fullname: Ito, Keiichi – sequence: 15 givenname: Kiyotaka surname: Toyoyama fullname: Toyoyama, Kiyotaka – sequence: 16 givenname: Satoru surname: Tateyama fullname: Tateyama, Satoru – sequence: 17 givenname: Takahiro surname: Mori fullname: Mori, Takahiro – sequence: 18 givenname: Takatsugu orcidid: 0000-0002-3933-8928 surname: Murata fullname: Murata, Takatsugu email: t_murata@rs.tus.ac.jp |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38160411$$D View this record in MEDLINE/PubMed |
BookMark | eNqNkM1KxDAQx4Mofj-BID0q0t1J2rTpURa_QPGwei5pOtVIN1mTFNk38Owj-iRm2XWPYi4zDL9_ZvgdkG1jDRJyQmFEgdGxVH5k3UuPIYwyBZkoyy2yTznL0hI42970BeyRA-_fAGicVLtkLxO0gJzSfVI-2SD7ZLow4RW99ontktglU_Tvgw7o5mgwOfv-_DpPH9A53fdaGm2OyE4ne4_H63pInq-vnia36f3jzd3k8j6VrOIhzUVJm67gUnWUNSyHtmwZB4kAKHLFqOKC0raFphPIi7Iq8jyTWKmmQcVKlR2Ss9W_c2ffB_ShnmmvsO-lQTv4mlVQgeBUQESzFaqc9d5hV8-dnkm3qCnUS2N1NFavjdVrYzF1ul4wNDNsN5lfRRG4WAEf2NjOK41G4QZbOi0YyymH-Ja0-D890UEGbc3EDibE6HgVXZ75Zgdnotg_b_8B47Kcug |
Cites_doi | 10.1002/tcr.201300022 10.1021/cr400685r 10.1021/jacs.9b05065 10.1002/chem.200500417 10.1038/NCHEM.2283 10.1021/acs.joc.8b02802 10.1021/jacs.3c01262 10.1021/ja012495d 10.1055/s-0029-1216922 10.1021/ol202403q 10.1016/S0040-4020(02)00734-2 10.1021/ja00203a027 10.1039/c39870001625 10.1038/nchem.2283 10.1021/ja00462a049 10.1055/s-1984-30848 10.5012/bkcs.1994.15.9.710 10.26434/chemrxiv-2022-0k1bz-v2 10.1016/S0040-4020(98)00400-1 10.1002/anie.197902393 10.1246/cl.1990.129 10.5059/yukigoseikyokaishi.53.987 10.1246/cl.1990.1455 |
ContentType | Journal Article |
Copyright | 2023 American Chemical Society |
Copyright_xml | – notice: 2023 American Chemical Society |
DBID | 1KM BLEPL BNZSX DTL NPM AAYXX CITATION 7X8 |
DOI | 10.1021/acs.orglett.3c03877 |
DatabaseName | Index Chemicus Web of Science Core Collection Web of Science - Science Citation Index Expanded - 2023 Science Citation Index Expanded PubMed CrossRef MEDLINE - Academic |
DatabaseTitle | Web of Science PubMed CrossRef MEDLINE - Academic |
DatabaseTitleList | Web of Science MEDLINE - Academic PubMed |
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: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Chemistry |
EISSN | 1523-7052 |
EndPage | 3331 |
ExternalDocumentID | 10_1021_acs_orglett_3c03877 38160411 001162241500001 c21845224 |
Genre | Journal Article |
GroupedDBID | --- -DZ -~X .K2 123 4.4 55A 5VS 6P2 7~N AABXI ABFRP ABJNI ABMVS ABQRX ABUCX ACGFS ACS ADHLV AEESW AENEX AFEFF AHGAQ ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH CS3 DU5 EBS ED~ F5P FDB GGK GNL IH9 IHE JG~ P2P RNS ROL TN5 UI2 VF5 VG9 W1F YNT 1KM 53G AAHBH AALRI AAXUO BLEPL CUPRZ DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED NPM AAYXX CITATION 7X8 |
ID | FETCH-LOGICAL-a295t-4871bf65acf12b240d7d250ae00e84c21c5811dd0bf8e56796443ae9cbbec27c3 |
IEDL.DBID | ACS |
ISICitedReferencesCount | 0 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=001162241500001 |
ISSN | 1523-7060 |
IngestDate | Sat Oct 26 05:32:01 EDT 2024 Fri Aug 23 04:10:26 EDT 2024 Sat Nov 02 12:30:41 EDT 2024 Wed Oct 30 11:06:48 EDT 2024 Fri Nov 08 20:05:53 EST 2024 Mon Apr 29 05:48:49 EDT 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 16 |
Keywords | ALDOL REACTIONS OLEFINS |
Language | English |
LinkModel | DirectLink |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-LOGICAL-a295t-4871bf65acf12b240d7d250ae00e84c21c5811dd0bf8e56796443ae9cbbec27c3 |
Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ORCID | 0000-0002-3933-8928 0000-0002-8749-2540 |
PMID | 38160411 |
PQID | 2909085180 |
PQPubID | 23479 |
PageCount | 5 |
ParticipantIDs | webofscience_primary_001162241500001 acs_journals_10_1021_acs_orglett_3c03877 proquest_miscellaneous_2909085180 pubmed_primary_38160411 crossref_primary_10_1021_acs_orglett_3c03877 webofscience_primary_001162241500001CitationCount |
PublicationCentury | 2000 |
PublicationDate | 2024-04-26 |
PublicationDateYYYYMMDD | 2024-04-26 |
PublicationDate_xml | – month: 04 year: 2024 text: 2024-04-26 day: 26 |
PublicationDecade | 2020 |
PublicationPlace | WASHINGTON |
PublicationPlace_xml | – name: WASHINGTON – name: United States |
PublicationTitle | Organic letters |
PublicationTitleAbbrev | ORG LETT |
PublicationTitleAlternate | Org. Lett |
PublicationYear | 2024 |
Publisher | American Chemical Society Amer Chemical Soc |
Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
References | Huang, JM (WOS:000177494700020) 2002; 58 MATSUDA, F (WOS:A1995TF04800006) 1995; 53 Lu, HH (WOS:000356805300014) 2015; 7 MOLANDER, GA (WOS:A1989AU57400027) 1989; 111 Shiina, I (WOS:000269924800010) 2009 MUKAIYAMA, T (WOS:A1990CK92600035) 1990 Sono, M (WOS:000296212200003) 2011; 13 KANG, HY (WOS:A1994PN88000007) 1994; 15 Condakes, ML (WOS:000454567900001) 2018; 83 Suwa (001162241500001.22) 2023 TSUJI, J (WOS:A1984SU80200001) 1984 KOBAYASHI, S (WOS:A1990DV84900056) 1990 GRIFFITH, WP (WOS:A1987K683400013) 1987 Burns, AS (WOS:000484082700004) 2019; 141 Birman, VB (WOS:000174469600004) 2002; 124 Shiina, I (WOS:000331876000013) 2014; 14 Akeboshi, T (WOS:000074088400010) 1998; 54 SEEBACH, D (WOS:A1979GU96800001) 1979; 18 Shiina, I (WOS:000233293100017) 2005; 11 MASAMUNE, S (WOS:A1977DV72000049) 1977; 99 Szostak, M (WOS:000337336500009) 2014; 114 Etling, C (WOS:000957580200001) 2023; 145 ref6/cit6 ref10/cit10d ref10/cit10e ref2/cit2e ref12/cit12 ref2/cit2d ref15/cit15 ref3/cit3b ref3/cit3c ref10/cit10a ref10/cit10b ref3/cit3a ref10/cit10c ref13/cit13 ref2/cit2c ref8/cit8 ref2/cit2b ref5/cit5 ref2/cit2a ref4/cit4 ref1/cit1 ref7/cit7 |
References_xml | – start-page: 129 year: 1990 ident: WOS:A1990CK92600035 article-title: CATALYTIC ASYMMETRIC ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES BY THE USE OF CHIRAL DIAMINE COORDINATED TIN(II) TRIFLATE publication-title: CHEMISTRY LETTERS contributor: fullname: MUKAIYAMA, T – start-page: 1455 year: 1990 ident: WOS:A1990DV84900056 article-title: THE EFFICIENT CATALYTIC ASYMMETRIC ALDOL-TYPE REACTION publication-title: CHEMISTRY LETTERS contributor: fullname: KOBAYASHI, S – volume: 99 start-page: 6756 year: 1977 ident: WOS:A1977DV72000049 article-title: ACTIVATION OF THIOL ESTERS - PARTIAL SYNTHESIS OF CYTOCHALASINS-A AND CYTOCHALASINS-B publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MASAMUNE, S – volume: 54 start-page: 7387 year: 1998 ident: WOS:000074088400010 article-title: A chemo-enzymatic elaboration of a quarternary chiral center: an alternative approach to the side chain of furaquinocin D publication-title: TETRAHEDRON contributor: fullname: Akeboshi, T – volume: 14 start-page: 144 year: 2014 ident: WOS:000331876000013 article-title: Asymmetric Mukaiyama Aldol Reactions Using Chiral Diamine-Coordinated Sn(II) Triflate: Development and Application to Natural Product Synthesis publication-title: CHEMICAL RECORD doi: 10.1002/tcr.201300022 contributor: fullname: Shiina, I – volume: 58 start-page: 6937 year: 2002 ident: WOS:000177494700020 article-title: Merrillianin, a unique seco-prezizaane-type sesquiterpene, and (6R)-pseudomajucin from Illicium merrillianum publication-title: TETRAHEDRON contributor: fullname: Huang, JM – start-page: 1625 year: 1987 ident: WOS:A1987K683400013 article-title: PREPARATION AND USE OF TETRA-NORMAL-BUTYLAMMONIUM PER-RUTHENATE (TBAP REAGENT) AND TETRA-NORMAL-PROPYLAMMONIUM PER-RUTHENATE (TPAP REAGENT) AS NEW CATALYTIC OXIDANTS FOR ALCOHOLS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: GRIFFITH, WP – volume: 18 start-page: 239 year: 1979 ident: WOS:A1979GU96800001 article-title: METHODS OF REACTIVITY UMPOLUNG publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH contributor: fullname: SEEBACH, D – volume: 15 start-page: 710 year: 1994 ident: WOS:A1994PN88000007 article-title: SAMARIUM(II) IODIDE PROMOTED INTRAMOLECULAR COUPLING BETWEEN CARBONYL GROUPS AND ACTIVATED OLEFINS UNDER STERICALLY CROWDED ENVIRONMENT publication-title: BULLETIN OF THE KOREAN CHEMICAL SOCIETY contributor: fullname: KANG, HY – volume: 114 start-page: 5959 year: 2014 ident: WOS:000337336500009 article-title: Cross-Coupling Reactions Using Samarium(II) Iodide publication-title: CHEMICAL REVIEWS doi: 10.1021/cr400685r contributor: fullname: Szostak, M – volume: 141 start-page: 13295 year: 2019 ident: WOS:000484082700004 article-title: Total Synthesis and Structure Revision of (-)-Illisimonin A, a Neuroprotective Sesquiterpenoid from the Fruits of Illicium simonsii publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.9b05065 contributor: fullname: Burns, AS – volume: 53 start-page: 987 year: 1995 ident: WOS:A1995TF04800006 article-title: HYDROXYL-DIRECTED CARBON-CARBON BOND FORMATION REACTIONS MEDIATED BY SAMARIUM(II) IODIDE publication-title: JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN contributor: fullname: MATSUDA, F – volume: 11 start-page: 6601 year: 2005 ident: WOS:000233293100017 article-title: Enantioselective total synthesis of octalactin a using asymmetric aldol reactions and a rapid lactonization to form a medium-sized ring publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200500417 contributor: fullname: Shiina, I – volume: 7 start-page: 604 year: 2015 ident: WOS:000356805300014 article-title: An eight-step gram-scale synthesis of (-)-jiadifenolide publication-title: NATURE CHEMISTRY doi: 10.1038/NCHEM.2283 contributor: fullname: Lu, HH – volume: 111 start-page: 8236 year: 1989 ident: WOS:A1989AU57400027 article-title: INTRAMOLECULAR REDUCTIVE COUPLING REACTIONS PROMOTED BY SAMARIUM DIIODIDE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MOLANDER, GA – start-page: 369 year: 1984 ident: WOS:A1984SU80200001 article-title: SYNTHETIC APPLICATIONS OF THE PALLADIUM-CATALYZED OXIDATION OF OLEFINS TO KETONES publication-title: SYNTHESIS-STUTTGART contributor: fullname: TSUJI, J – volume: 83 start-page: 14843 year: 2018 ident: WOS:000454567900001 article-title: Contemporary Synthetic Strategies toward seco-Prezizaane Sesquiterpenes from Illicium Species publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.8b02802 contributor: fullname: Condakes, ML – volume: 145 start-page: 7021 year: 2023 ident: WOS:000957580200001 article-title: Asymmetric Total Synthesis of Illisimonin A publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.3c01262 contributor: fullname: Etling, C – year: 2023 ident: 001162241500001.22 article-title: First TotalSynthesisof (-)-Merrillianin publication-title: ChemRxiv contributor: fullname: Suwa – volume: 124 start-page: 2080 year: 2002 ident: WOS:000174469600004 article-title: The total synthesis of (±)-merrilactone A publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja012495d contributor: fullname: Birman, VB – start-page: 2915 year: 2009 ident: WOS:000269924800010 article-title: Enantioselective Aldol Reaction of Tetrasubstituted Ketene Silyl Acetals with Achiral Aldehydes for the Construction of Asymmetric Tertiary Alcohols: An Application for the Divergent Total Syntheses of Buergerinins F and G publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-0029-1216922 contributor: fullname: Shiina, I – volume: 13 start-page: 5720 year: 2011 ident: WOS:000296212200003 article-title: First Direct Evidence of Radical Intermediates in Samarium Diiodide Induced Cyclization by ESR Spectra publication-title: ORGANIC LETTERS doi: 10.1021/ol202403q contributor: fullname: Sono, M – ident: ref1/cit1 doi: 10.1016/S0040-4020(02)00734-2 – ident: ref10/cit10d doi: 10.1021/ja00203a027 – ident: ref12/cit12 doi: 10.1055/s-0029-1216922 – ident: ref7/cit7 doi: 10.1002/chem.200500417 – ident: ref10/cit10b doi: 10.1021/cr400685r – ident: ref6/cit6 doi: 10.1039/c39870001625 – ident: ref2/cit2b doi: 10.1038/nchem.2283 – ident: ref4/cit4 doi: 10.1021/ja00462a049 – ident: ref2/cit2e doi: 10.1021/jacs.3c01262 – ident: ref13/cit13 doi: 10.1055/s-1984-30848 – ident: ref2/cit2c doi: 10.1021/acs.joc.8b02802 – ident: ref10/cit10e doi: 10.5012/bkcs.1994.15.9.710 – ident: ref15/cit15 doi: 10.26434/chemrxiv-2022-0k1bz-v2 – ident: ref10/cit10c doi: 10.1021/ol202403q – ident: ref5/cit5 doi: 10.1016/S0040-4020(98)00400-1 – ident: ref8/cit8 doi: 10.1002/anie.197902393 – ident: ref2/cit2d doi: 10.1021/jacs.9b05065 – ident: ref3/cit3c doi: 10.1002/tcr.201300022 – ident: ref2/cit2a doi: 10.1021/ja012495d – ident: ref3/cit3a doi: 10.1246/cl.1990.129 – ident: ref10/cit10a doi: 10.5059/yukigoseikyokaishi.53.987 – ident: ref3/cit3b doi: 10.1246/cl.1990.1455 |
SSID | ssj0011529 |
Score | 2.4893918 |
Snippet | The first total synthesis of (−)-merrillianin (1), which is a natural sesquiterpene with a tricyclic structure having a cyclopentane ring and five- and... The first total synthesis of (-)-merrillianin (1), which is a natural sesquiterpene with a tricyclic structure having a cyclopentane ring and five- and... The first total synthesis of (-)-merrillianin ( ), which is a natural sesquiterpene with a tricyclic structure having a cyclopentane ring and five- and... |
Source | Web of Science |
SourceID | proquest crossref pubmed webofscience acs |
SourceType | Aggregation Database Index Database Enrichment Source Publisher |
StartPage | 3327 |
SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
Title | Total Synthesis of the Sesquiterpene (−)-Merrillianin |
URI | http://dx.doi.org/10.1021/acs.orglett.3c03877 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001162241500001 https://www.ncbi.nlm.nih.gov/pubmed/38160411 https://search.proquest.com/docview/2909085180 |
Volume | 26 |
WOS | 001162241500001 |
WOSCitedRecordID | wos001162241500001 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3JTuQwEC0xcGAuLLNA2JSRODDSuImXJPYRtUAICS4NErfIdmwJjZQGkj7AF3DmE_kSyumkxQAa9S2LZamq7NSLn-sZYF9LBPZee2KMcERYqYk0yhPBmUwMVapsT547v8hOr8TZdXr9plj9HYPP6KG2dbhHK5oBt4Ftzb_AEstxegQkNBzNSANMRaqVR2WcBFGYXmTo805COrL1v-noA8b8NB21qedkFS76Ap7pjpO_g0ljBvbxo57jfFatwUoHQuOj6ahZhwVXfYPlYX_223fIL8cIyuPRQ4X4sL6p47GP8SoeufpuEoqWb_ETGR-8PD3_JudB2zEs2lQ31Q-4Ojm-HJ6S7ogFoplKG4K_K9T4LNXWU2Ywu5d5iaBIuyRxUlhGbSopLcvEeOnSsOYkBNdOWYOxZ7nlP2GxGlduE2JZyoxmJuM648LzUiMy8kE6p5RcOJVHcIBGF90UqYuW_Wa0CA87TxSdJyL40weluJ2Kbvy_-a8-cAX6KTAeunLjSV0wlaiAKWUSwcY0orMOA2OaCEoj2H8b4tn7lqJqAU7LgERA52k27JTVg6JAszW_ydvwlSFcCjwVy3ZgsbmfuF2EO43Zawf5K1f6-jw |
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/eLvHCXMwlV3LbtQwFL2CsiibQssrtJQgdVEkPMSPJPYSjagG6HQzM1J3ke3YUlUpU5rMAr6ANZ_Il3DtyUyBVqjdRY5l-fo6OSc-8THAgZZI7L32xBjhiLBSE2mUJ4IzmRmqVB1PnhufFKOZ-Hyan_abwsJeGOxEiy21UcS_cheg7_syDKYbcBtE1_I-PMhLhMxAiIaTtXaAiKSiSyrjJHjDrLyGbm4koJJt_0ala1TzRlSKCHT0CGbrvscfT84Hi84M7Pd_bB3vGtxj2OopafphOYe24Z5rdmBzuDoJ7gmU0zlS9HTyrUG22J616dyneJVOXPt1EbYwX-ALMz389ePnWzIOTo9hCac5a57C7OjjdDgi_YELRDOVdwQ_XqjxRa6tp8wg1tdljRRJuyxzUlhGbS4prevMeOnysAIlBNdOWYMzgZWWP4ONZt64F5DKWha0MAXXBRee1xp5kg9GOrXkwqkygUMMuuofmLaKWjijVSjsR6LqRyKBd6vcVBdLC47_V3-zyl-F4xT0D924-aKtmMpUYJgyS-D5MrHrBoN-mglKEzj4M9Pr-1GwinQn6iEJ0NtUG_Y-68FfoHt5-5Bfw-ZoOj6ujj-dfNmFhwyJVFCwWLEHG93lwr1CItSZ_TjvfwO9GAKw |
linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Jb9QwFH4qRQIu7EtYg9RDkfAQL0nsYzUwKksrpGmlcoq8ShVSZiCZA_wCzvxEfgnPnmTEUqGKW-RYlt97dt4Xf_ZngB0tEdgHHYgxwhNhpSbSqEAEZ7IwVCmXbp47OKz2j8Wbk_JkC-R4FgY70WFLXSLx46xeujAoDNAXQzka1E-4jcRrfQEuljVNBO3edL7hDzArqaSUyjiJ-jCj3tDZjcTMZLvfM9NfcPPMzJSy0OwafNj0P20--ThZ9WZiv_4h7fg_Bl6HqwM0zffWY-kGbPn2JlyejjfC3YL6aIFQPZ9_aRE1dqddvgg5PuVz331axaPMS_xw5rs_vn1_Rg6i4mNcymlP29twPHt1NN0nw8ULRDNV9gR_YqgJValtoMxgzne1Q6ikfVF4KSyjtpSUOleYIH0ZV6KE4Nora3BEsNryO7DdLlp_D3LpZEUrU3FdcRG404iXQhTUcZILr-oMdtHoZpg4XZM4cUabWDh4ohk8kcHzMT7Nci3F8e_qT8cYNuinyIPo1i9WXcNUoSLSlEUGd9fB3TQYedRCUJrBzq_R3rxPxFWCPYkXyYCep9p00FuPOgP9_fOb_AQuvX85a969Pnz7AK4wxFORyGLVQ9juP6_8I8RDvXmchv5PBxQFKg |
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=Total+Synthesis+of+the+Sesquiterpene+%28%E2%88%92%29-Merrillianin&rft.jtitle=Organic+letters&rft.au=Shiina%2C+Isamu&rft.au=Iizumi%2C+Takashi&rft.au=Taniguchi%2C+Saori&rft.au=Sugimoto%2C+Masuhiro&rft.date=2024-04-26&rft.pub=American+Chemical+Society&rft.issn=1523-7060&rft.eissn=1523-7052&rft.volume=26&rft.issue=16&rft.spage=3327&rft.epage=3331&rft_id=info:doi/10.1021%2Facs.orglett.3c03877&rft.externalDocID=c21845224 |
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 |