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

Nelson, Hosea M. and Murakami, Kei and Virgil, Scott C. and Stoltz, Brian M. (2011) A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D. Angewandte Chemie International Edition, 50 (16). pp. 3688-3691. ISSN 1433-7851. https://resolver.caltech.edu/CaltechAUTHORS:20110404-113128218

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201008003DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201008003/abstractPublisherArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: December 18, 2010. Article first published online: 25 Mar. 2011. 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.
Funders:
Funding AgencyGrant Number
King Abdullah University of Science and Technology (KAUST)KUS-11-006-02
NSFUNSPECIFIED
Ford FoundationUNSPECIFIED
Japan Society for the Promotion of Science (JSPS)UNSPECIFIED
AmgenUNSPECIFIED
AbbottUNSPECIFIED
Boehringer IngelheimUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
NSFCHE-0639094
Subject Keywords:acetylides; C[BOND]C coupling reactions; Claisen rearrangement; Diels–Alder reaction; natural product synthesis
Issue or Number:16
Record Number:CaltechAUTHORS:20110404-113128218
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20110404-113128218
Official Citation:Nelson, H. M., Murakami, K., Virgil, S. C. and Stoltz, B. M. (2011), A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D. Angewandte Chemie International Edition, 50: 3688–3691. doi: 10.1002/anie.201008003
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:23240
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:12 Apr 2011 16:37
Last Modified:03 Oct 2019 02:44

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