The enantioselective total synthesis of laurendecumallene B.

Chemical Science
Cooper A TaylorScott A Snyder

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.

References

Jun 29, 2002·Journal of Natural Products·Minoru SuzukiKimiko Kobayashi
Sep 20, 2008·Organic Letters·Cyrille SabotSylvain Canesi
Sep 17, 2009·Angewandte Chemie·Scott A Snyder, Daniel S Treitler
Mar 27, 2010·Organic Letters·Ock-Youm Jeon, Erick M Carreira
Sep 17, 2011·Journal of the American Chemical Society·Scott A SnyderWesley Sattler
Aug 24, 2012·The Journal of Organic Chemistry·Santosh KeshipeddyAmy R Howell
Mar 2, 2013·Chemical Reviews·Bin-Gui WangJian-Chun Zhao
Feb 8, 2018·Journal of the American Chemical Society·Andreas M ArnoldTanja Gulder
Sep 29, 2019·Journal of the American Chemical Society·Hau Sun Sam ChanJonathan W Burton

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Methods Mentioned

BETA
NMR
X-ray

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