A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D

Handle URI:
http://hdl.handle.net/10754/597275
Title:
A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D
Authors:
Nelson, Hosea M.; Murakami, Kei; Virgil, Scott C.; Stoltz, Brian M.
Abstract:
(Figure Presented) 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. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.
Citation:
Nelson HM, Murakami K, Virgil SC, Stoltz BM (2011) A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D. Angew Chem Int Ed 50: 3688–3691. Available: http://dx.doi.org/10.1002/anie.201008003.
Publisher:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
KAUST Grant Number:
KUS-11-006-02
Issue Date:
25-Mar-2011
DOI:
10.1002/anie.201008003
PubMed ID:
21442697
Type:
Article
ISSN:
1433-7851
Sponsors:
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 1a. The Bruker KAPPA APEXII X-ray diffractometer used in this study was purchased through an NSF CRIF:MU award to Caltech, CHE-0639094.
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorNelson, Hosea M.en
dc.contributor.authorMurakami, Keien
dc.contributor.authorVirgil, Scott C.en
dc.contributor.authorStoltz, Brian M.en
dc.date.accessioned2016-02-25T12:29:36Zen
dc.date.available2016-02-25T12:29:36Zen
dc.date.issued2011-03-25en
dc.identifier.citationNelson HM, Murakami K, Virgil SC, Stoltz BM (2011) A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D. Angew Chem Int Ed 50: 3688–3691. Available: http://dx.doi.org/10.1002/anie.201008003.en
dc.identifier.issn1433-7851en
dc.identifier.pmid21442697en
dc.identifier.doi10.1002/anie.201008003en
dc.identifier.urihttp://hdl.handle.net/10754/597275en
dc.description.abstract(Figure Presented) 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. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.en
dc.description.sponsorshipThis 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 1a. The Bruker KAPPA APEXII X-ray diffractometer used in this study was purchased through an NSF CRIF:MU award to Caltech, CHE-0639094.en
dc.publisherWiley-Blackwellen
dc.subjectAcetylidesen
dc.subjectC-C coupling reactionsen
dc.subjectClaisen rearrangementen
dc.subjectDiels-Alder reactionen
dc.subjectNatural product synthesisen
dc.titleA General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide Den
dc.typeArticleen
dc.identifier.journalAngewandte Chemie International Editionen
dc.contributor.institutionCalifornia Institute of Technology, Pasadena, United Statesen
kaust.grant.numberKUS-11-006-02en

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