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

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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

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Publication details

The article was received on 22 Sep 2018, accepted on 03 Dec 2018 and first published on 03 Dec 2018


Article type: Communication
DOI: 10.1039/C8OB02364F
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Enantioselective synthesis and absolute configuration determination of hydroxywilfordic acid in sesquiterpene pyridine alkaloids

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

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