Issue 1, 2019

Enantioselective synthesis and absolute configuration determination of hydroxywilfordic acid in sesquiterpene pyridine alkaloids

Abstract

An enantioselective synthetic route to hydroxywilfordic acid, a key subunit of sesquiterpene pyridine alkaloids such as wilfortrine, was developed. Asymmetric cyanation using Jacobsen's (R,R)-amino-thiourea and hydrolysis were performed to afford chiral α-hydroxy-α-methyl acid as the (S)-isomer. Naturally derived hydroxywilfordate prepared by methanolysis of wilfortrine was found to be the (R)-isomer upon comparison with the synthetic compound.

Graphical abstract: Enantioselective synthesis and absolute configuration determination of hydroxywilfordic acid in sesquiterpene pyridine alkaloids

Supplementary files

Article information

Article type
Communication
Submitted
22 Қыр. 2018
Accepted
03 Жел. 2018
First published
03 Жел. 2018

Org. Biomol. Chem., 2019,17, 44-48

Enantioselective synthesis and absolute configuration determination of hydroxywilfordic acid in sesquiterpene pyridine alkaloids

Y. Yuan, J. Jung and S. Seo, Org. Biomol. Chem., 2019, 17, 44 DOI: 10.1039/C8OB02364F

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