Total synthesis of (S)-equol.
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].
Heemstra
Jennifer M
JM
Obiter Research, LLC, 2004 South Wright Street Extended, Suite 110, Urbana, Illinois 61802, USA.
Kerrigan
Sean A
SA
Doerge
Daniel R
DR
Helferich
William G
WG
Boulanger
William A
WA
D000478:Alkylation; D002839:Chromans / Q000138:chemical synthesis; D002851:Chromatography, High Pressure Liquid; D060754:Equol; D004987:Ethers / Q000138:chemical synthesis; D007202:Indicators and Reagents; D007529:Isoflavones / Q000138:chemical synthesis*; D013237:Stereoisomerism
C007610:4',7-dihydroxy-3,4-dihydroisoflavone; D002839:Chromans; D004987:Ethers; D007202:Indicators and Reagents; D007529:Isoflavones; D060754:Equol