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Merck

Total synthesis of (S)-equol.

Organic letters (2006-11-17)
Jennifer M Heemstra, Sean A Kerrigan, Daniel R Doerge, William G Helferich, William A Boulanger
ABSTRACT

The first enantioselective total synthesis of (S)-equol is reported. The described route relies on an Evans alkylation to form the stereocenter and an intramolecular Buchwald etherification to generate the chroman ring. Key features of this method include its brevity, its scalability, and the low cost of starting materials. [reaction: see text].

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(S)-4-Benzyl-2-oxazolidinone, 99%