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

par Chopin, Nathalie;Couty, François;Evano, Gwilherm
Référence Letters in Organic Chemistry, 7, 5, page (353-359)
Publication Publié, 2010

Article révisé par les pairs

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Résumé :

An efficient synthesis of the azetidinyl-thiazoline fragment of the antifungal and cytotoxic macrolides vioprolides A and C is reported. Key steps of the ynthesis 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.