Tetrahedron

Synthesis of the enantiomers of 5-hexadecanolide, the pheromone of the queen of the oriental hornet, Vespa orientalis, employing enzymic resolution of (±)-2- …

K Mori, T Otsuka

Index: Mori, Kenji; Otsuka, Tatsuya Tetrahedron, 1985 , vol. 41, # 3 p. 547 - 551

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Citation Number: 52

Abstract

Optical resolution of (±)-2-chloroacetylaminotridecanoic acid with amino acylase gave (S)-2- aminotridecanoic add, which was converted into highly optically pure (S)-5-hexadecanolide (the pheromone of Vespa orientalls). Similarly (R)-2-chloroacetylammotridecanoic acid recovered after the enzymic hydrolysis yielded (R)-5-hexadecanolide. The existing methods for the preparation of the enantiomers of 5-hexadecanolide were critically surveyed to ...