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The Enantioselective Total Synthesis of Laurendecumallene B

Abstract

For decades, the Laurencia family of halogenated C15-acetogenins has served as a valuable testing ground for the prowess of chemical synthesis, particularly as it relates to generating functionalized 8-membered bromoethers. Herein, we show that a readily modified and predictable approach that generates such rings and an array of attendant stereocenters via a bromenium-induced cyclization/ring-expansion process can be used to synthesize laurendecumallene B and determine the configuration of two of its previously unassigned stereocenters. In particular, this work highlights how the use of the bromenium source BDSB (Et2SBr•SbCl5Br) in non-conventional solvents is essential to generating much of the target’s complexity in optimal yields and stereoselectivity. Moreover, the final structural assignment of laurendecumallene B reveals that it has one element of bromine-based chirality that, to the best of our knowledge, is not shared with any other member of the class.

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Article information


Submitted
04 Dec 2019
Accepted
05 Feb 2020
First published
06 Feb 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Accepted Manuscript
Article type
Edge Article

The Enantioselective Total Synthesis of Laurendecumallene B

C. A. Taylor, Y. Zhang and S. A. Snyder, Chem. Sci., 2020, Accepted Manuscript , DOI: 10.1039/C9SC06116A

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