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Total Syntheses of (-)-Transtaganolide A, (+)-Transtaganolide B, (+)-Transtaganolide C, and (-)-Transtaganolide D and Biosynthetic Implications

Nelson, Hosea M. and Gordon, Jonny R. and Virgil, Scott C. and Stoltz, Brian M. (2013) Total Syntheses of (-)-Transtaganolide A, (+)-Transtaganolide B, (+)-Transtaganolide C, and (-)-Transtaganolide D and Biosynthetic Implications. Angewandte Chemie International Edition, 52 (26). pp. 6699-6703. ISSN 1433-7851. PMCID PMC3825171.

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‘Dibal'lin’ on a budget: The enantioselective total syntheses of transtaganolides A–D are rapidly achieved by a highly diastereoselective Ireland–Claisen/Diels–Alder cascade reaction of an enantioenriched geraniol derivative (see scheme). Based on X-ray diffraction data, the absolute configuration of these metabolites is established and discussed within the context of existing biosynthetic hypotheses.

Item Type:Article
Related URLs:
URLURL TypeDescription DOIArticle CentralArticle
Nelson, Hosea M.0000-0002-4666-2793
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: February 11, 2013; Published online: May 16, 2013. The authors wish to thank the NSF and Ford Foundation (predoctoral fellowships to H.M.N.), Amgen, Abbott, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for financial support. Prof. Giovanni Appendino is acknowledged for providing authentic samples of basiliolide B. Dr. Kei Murakami is acknowledged for his contribution to the preparation of racemic transtaganolides C and D. Kelly Kim and Alexander Goldberg are gratefully acknowledged for assistance in manuscript preparation. Dr. Nolan McDougal is acknowledged for useful discussions regarding biosynthesis. Larry Henling is acknowledged for X-ray analysis of 33. Dr. David VanderVelde is acknowledged for NMR assistance. The authors wish to thank NIH-NIGMS (R01GM080269) for financial support. The Bruker KAPPA APEXII Xray diffractometer used in this study was purchased through an NSF CRIF:MU award to Caltech (CHE-0639094).
Funding AgencyGrant Number
NSF Predoctoral FellowshipUNSPECIFIED
Ford FoundationUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
Subject Keywords:biomimetic synthesis; biosynthesis; cycloaddition; rearrangement; total synthesis
Issue or Number:26
PubMed Central ID:PMC3825171
Record Number:CaltechAUTHORS:20130809-132636851
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Official Citation:Nelson, H. M., Gordon, J. R., Virgil, S. C. and Stoltz, B. M. (2013), Total Syntheses of (−)-Transtaganolide A, (+)-Transtaganolide B, (+)-Transtaganolide C, and (−)-Transtaganolide D and Biosynthetic Implications . Angew. Chem. Int. Ed., 52: 6699–6703. doi: 10.1002/anie.201301212
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:39844
Deposited By: Tony Diaz
Deposited On:12 Aug 2013 20:57
Last Modified:09 Mar 2020 13:19

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