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.; Murakami, Kei; Virgil, Scott C.; Stoltz, Brian M.

Type

Article

Authors

Nelson, Hosea M.
Murakami, Kei
Virgil, Scott C.
Stoltz, Brian M.

KAUST Grant Number

KUS-11-006-02

Date

2011-03-25

Online Publication Date

2011-03-25

Print Publication Date

2011-04-11

Permanent link to this record

http://hdl.handle.net/10754/597275

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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.

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.