4 years ago

Enantioselective Chemical Syntheses of the Furanosteroids (−)-Viridin and (−)-Viridiol

Enantioselective Chemical Syntheses of the Furanosteroids (−)-Viridin and (−)-Viridiol
Carlos A. Guerrero, Jeffrey D. Ng, Alexander R. Abela, Matthew Del Bel
Herein we describe concise enantioselective chemical syntheses of (−)-viridin and (−)-viridiol. Our convergent approach couples two achiral fragments of similar complexity and employs an enantioselective intramolecular Heck reaction to set the absolute stereochemical configuration of an all-carbon quaternary stereocenter. To complete the syntheses of these base- and nucleophile-sensitive natural products, we conduct carefully orchestrated site- and diastereoselective oxidations and other transformations. Our work is the first to generate these targets as single enantiomers.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b02829

DOI: 10.1021/jacs.7b02829

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