期刊
CHEMICAL SCIENCE
卷 11, 期 11, 页码 3036-3041出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc06116a
关键词
-
资金
- University of Chicago
- National Institutes of Health [T32 GM08720]
For decades, the Laurencia family of halogenated C-15-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 center dot 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.
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