A Short Diastereoselective Total Synthesis of (±)-Vibralactone | Zendy

Alexander J. Leeder | Zendy; Robert J. Heap | Zendy; Lynda J. Brown | Zendy; Xavier Franck | Zendy; Richard C. D. Brown | Zendy

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A Short Diastereoselective Total Synthesis of (±)-Vibralactone

Author(s) -

Alexander J. Leeder,

Robert J. Heap,

Lynda J. Brown,

Xavier Franck,

Richard C. D. Brown

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b03007

Subject(s) - chemistry , total synthesis , alkene , yield (engineering) , wacker process , aldehyde , malonic acid , quaternary carbon , catalysis , organic chemistry , combinatorial chemistry , stereochemistry , enantioselective synthesis , palladium , materials science , metallurgy

A total synthesis of the (±)-vibralactone has been achieved in 11 steps and 16% overall yield from malonic acid. Key steps include a highly diastereoselective allylation of an α-formyl ester containing an all carbon α-quaternary center, a Pd-catalyzed deallylative β-lactonization, and an aldehyde-selective Wacker oxidation of a terminal alkene.

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