Issue 11, 2020

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 in 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.

Graphical abstract: The enantioselective total synthesis of laurendecumallene B

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2020,11, 3036-3041

The enantioselective total synthesis of laurendecumallene B

C. A. Taylor, Y. Zhang and S. A. Snyder, Chem. Sci., 2020, 11, 3036 DOI: 10.1039/C9SC06116A

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