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Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (−)-disparlure

✍ Scribed by Sadao Tsuboi; Nobuyuki Yamafuji; Masanori Utaka

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 289 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(96)00529-0

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✦ Synopsis

Reduction of 3-chloro-2-oxoalkanoates 1 with NaBH4 gave predominantly syn-3-chloro-2-hydroxyalkanoates 2 (synlanti=9119-9911) in 50--97% yields. Resolution of syn-2 by lipase-catalyzed transesterification gave (2S,3S)-2 and (2R,3R)-2-acetoxy-3chloroalkanoates (2R,3R)-3. Total synthesis of (-)-disparlure, the pheromone of the gypsy moth was established from (2S,3S)-2g via 4 steps in 34.9% overall yield. (~)

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