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Synthesis 1992; 1992(10): 1007-1012
DOI: 10.1055/s-1992-26290
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Pheromone Synthesis; CXXXIX.1 Enzymatic Preparation of (2S,3R)-4-Acetoxy-2,3-epoxybutan-1-ol and Its Conversion to the Epoxy Pheromones of the Gypsy Moth and the Ruby Tiger Moth

Jean-Luc Brevet* , Kenji Mori
  • *Department of Agricultural Chemistry, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113, Japan
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Publication Date:
17 September 2002 (online)

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Pig pancreatic lipase-catalyzed asymmetric hydrolysis of 1, 4-diacet-oxy-cis-2,3-epoxybutane yielded (2S,3R) -4-acetoxy-2,3-epoxybu-tan-1-ol, which was converted to two naturally occurring epoxides: the gypsy moth pheromone, disparlure [(7R,8S)-7,8-epoxy-2-methyloctadecane] and the ruby tiger moth pheromone [(6Z,9S,10R) -9,10-epoxy-6-henicosene].