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Published June 24, 2013 | Accepted Version + Supplemental Material
Journal Article Open

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


'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.

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).

Attached Files

Accepted Version - nihms523187.pdf

Supplemental Material - anie_201301212_sm_miscellaneous_information.pdf


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August 22, 2023
October 24, 2023