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 Sep 2018
Accepted
03 Dez 2018
First published
03 Dez 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements