A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi‐8‐Basiliolide B, Transtaganolide C, and Transtaganolide D
Identifieur interne : 000549 ( Main/Corpus ); précédent : 000548; suivant : 000550A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi‐8‐Basiliolide B, Transtaganolide C, and Transtaganolide D
Auteurs : Hosea M. Nelson ; Kei Murakami ; Virgil ; StoltzSource :
- Angewandte Chemie International Edition [ 1433-7851 ] ; 2011-04-11.
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Abstract
In a flash: The total synthesis of transtaganolide and basiliolide natural products is achieved in three steps from achiral, monocyclic esters (see scheme). Featured in the syntheses are an Ireland‐Claisen/Diels–Alder cascade and a novel methoxyacetylide coupling/cyclization sequence.
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DOI: 10.1002/anie.201008003
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ISTEX:CD3B53237A45817B5CC2AD1E39CA98529D6F8030Le document en format XML
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KGaA, Weinheim</p></availability><date>2011</date></publicationStmt><notesStmt><note type="content">*This publication is based on work supported by Award No. KUS‐11‐006‐02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank the NSF and Ford Foundation (predoctoral fellowship to H.M.N.), the Japan Society for the Promotion of Science (fellowship for K.M.), Amgen, Abbott, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for financial support. Dr. J. T. Mohr is gratefully acknowledged for useful discussions. Larry Henling and Dr. Michael Day are acknowledged for X‐ray analysis of 1 a. 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California Boulevard, MC 101‐20, Pasadena, CA 91125 (USA)</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="termsOfAddress">Prof. Dr.</namePart><namePart type="family">Stoltz</namePart><affiliation>Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 101‐20, Pasadena, CA 91125 (USA)</affiliation><description>Correspondence: Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 101‐20, Pasadena, CA 91125 (USA)</description><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="brief-communication" displayLabel="shortCommunication"></genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2011-04-11</dateIssued><dateCaptured encoding="w3cdtf">2010-12-18</dateCaptured><copyrightDate encoding="w3cdtf">2011</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType><extent unit="figures">7</extent><extent unit="references">41</extent></physicalDescription><abstract>In a flash: The total synthesis of transtaganolide and basiliolide natural products is achieved in three steps from achiral, monocyclic esters (see scheme). Featured in the syntheses are an Ireland‐Claisen/Diels–Alder cascade and a novel methoxyacetylide coupling/cyclization sequence.</abstract><note type="content">*This publication is based on work supported by Award No. KUS‐11‐006‐02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank the NSF and Ford Foundation (predoctoral fellowship to H.M.N.), the Japan Society for the Promotion of Science (fellowship for K.M.), Amgen, Abbott, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for financial support. Dr. J. T. Mohr is gratefully acknowledged for useful discussions. Larry Henling and Dr. Michael Day are acknowledged for X‐ray analysis of 1 a. The Bruker KAPPA APEXII X‐ray diffractometer used in this study was purchased through an NSF CRIF:MU award to Caltech, CHE‐0639094.</note><note type="funding">King Abdullah University of Science and Technology (KAUST)</note><note type="funding">NSF</note><subject lang="en"><genre>keywords</genre><topic>acetylides</topic><topic>CC coupling reactions</topic><topic>Claisen rearrangement</topic><topic>Diels–Alder reaction</topic><topic>natural product synthesis</topic></subject><relatedItem type="host"><titleInfo><title>Angewandte Chemie International Edition</title></titleInfo><titleInfo type="abbreviated"><title>Angew. Chem. Int. Ed.</title></titleInfo><genre type="journal">journal</genre><note type="content"> Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer‐reviewed, but not copy‐edited or typeset. They are made available as submitted by the authors.Supporting Info Item: miscellaneous_information - </note><subject><genre>article-category</genre><topic>Communication</topic></subject><identifier type="ISSN">1433-7851</identifier><identifier type="eISSN">1521-3773</identifier><identifier type="DOI">10.1002/(ISSN)1521-3773</identifier><identifier type="PublisherID">ANIE</identifier><part><date>2011</date><detail type="volume"><caption>vol.</caption><number>50</number></detail><detail type="issue"><caption>no.</caption><number>16</number></detail><extent unit="pages"><start>3688</start><end>3691</end><total>4</total></extent></part></relatedItem><identifier type="istex">CD3B53237A45817B5CC2AD1E39CA98529D6F8030</identifier><identifier type="DOI">10.1002/anie.201008003</identifier><identifier type="ArticleID">ANIE201008003</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. 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|texte= A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi‐8‐Basiliolide B, Transtaganolide C, and Transtaganolide D
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