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

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

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.

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.

Attached Files

Supplemental Material - anie_201008003_sm_miscellaneous_information.pdf

Files

anie_201008003_sm_miscellaneous_information.pdf

Files (10.6 MB)

Name	Size	Download all
anie_201008003_sm_miscellaneous_information.pdf md5:0e54b3ab62526967100cac4f2d2e44df	10.6 MB	Preview Download

Additional details

	All versions	This version
Views	0	0
Downloads	0	0
Data volume	0 Bytes	0 Bytes