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 http://resolver.caltech.edu/CaltechAUTHORS:20110504-113455454
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Abstract
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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| Additional Information: | © 2011 Wiley VCH Verlag GmbH & Co. KGaA, Weinheim. Issue published online: 5 April 2011; Article first published online: 25 March 2011; Manuscript Received: 18 December 2010. 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. | ||||||||||||||||||||||
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| Subject Keywords: | acetylides; C[BOND]C coupling reactions; Claisen rearrangement; Diels–Alder reaction; natural product synthesis | ||||||||||||||||||||||
| Record Number: | CaltechAUTHORS:20110504-113455454 | ||||||||||||||||||||||
| Persistent URL: | http://resolver.caltech.edu/CaltechAUTHORS:20110504-113455454 | ||||||||||||||||||||||
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| 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: | 23552 | ||||||||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||||||||
| Deposited By: | Jason Perez | ||||||||||||||||||||||
| Deposited On: | 04 May 2011 20:09 | ||||||||||||||||||||||
| Last Modified: | 04 May 2011 20:09 |
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