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A cross-metathesis approach to novel pantothenamide derivatives.

ABSTRACT: Pantothenamides are known for their in vitro antimicrobial activity. Our group has previously reported a new stereoselective route to access derivatives modified at the geminal dimethyl moiety. This route however fails in the addition of large substituents. Here we report a new synthetic route that exploits the known allyl derivative, allowing for the installation of larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in human blood.

SUBMITTER: Guan J

PROVIDER: S-EPMC4902030 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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A cross-metathesis approach to novel pantothenamide derivatives.

Guan Jinming J Hachey Matthew M Puri Lekha L Howieson Vanessa V Saliba Kevin J KJ Auclair Karine K

Beilstein journal of organic chemistry 20160513

Pantothenamides are known for their in vitro antimicrobial activity. Our group has previously reported a new stereoselective route to access derivatives modified at the geminal dimethyl moiety. This route however fails in the addition of large substituents. Here we report a new synthetic route that exploits the known allyl derivative, allowing for the installation of larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in hum ...[more]

PMID: 27340487

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