Synthesis of the Azetidinyl-Thiazoline Fragment of Vioprolides A and C

Nathalie      Chopin; Francois      Couty; Gwilherm      Evano

doi:10.2174/157017810791514814

Abstract

An efficient synthesis of the azetidinyl-thiazoline fragment of the antifungal and cytotoxic macrolides vioprolides A and C is reported. Key steps of the synthesis include formation of the thiazoline by condensation of N-Alloc- trans (2S,4R)-4-methylazetidine-2-carbonitrile with L-cysteine and formation of the four-membered ring by intramolecular alkylation of a suitably protected N-Alloc derivative prepared from (R)-alaninol.

Keywords: Azetidines, natural products, antifungal metabolites

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Letters in Organic Chemistry

Title: Synthesis of the Azetidinyl-Thiazoline Fragment of Vioprolides A and C

Volume: 7 Issue: 5

Author(s): Nathalie Chopin, Francois Couty and Gwilherm Evano

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Keywords: Azetidines, natural products, antifungal metabolites

Abstract: An efficient synthesis of the azetidinyl-thiazoline fragment of the antifungal and cytotoxic macrolides vioprolides A and C is reported. Key steps of the synthesis include formation of the thiazoline by condensation of N-Alloc- trans (2S,4R)-4-methylazetidine-2-carbonitrile with L-cysteine and formation of the four-membered ring by intramolecular alkylation of a suitably protected N-Alloc derivative prepared from (R)-alaninol.

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Chopin Nathalie, Couty Francois and Evano Gwilherm, Synthesis of the Azetidinyl-Thiazoline Fragment of Vioprolides A and C, Letters in Organic Chemistry 2010; 7 (5) . https://dx.doi.org/10.2174/157017810791514814