Reinvestigation of base-catalyzed condensation of ethyl .ALPHA.,.ALPHA.-dichloroacetoacetate with aldehydes. A new synthesis of (.+-.)-disparlure.

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概要

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• The titled reaction gave ethyl 2-chloro-2,3-epoxyalkanoates (<B>2</B>) and ethyl 3-chloro-2-oxoalkanoates in improved yields. The structure of the by-product was revised as 1,5-dichloro-4,8-dialkyltricyclo[5.1.0.0<SUP>3,5</SUP>]octane-2,6-dione by means of the <SUP>13</SUP>C–<SUP>1</SUP>H two-dimensional NMR spectrum and an X-ray crystallographic analysis. Compound <B>2</B> was applied to the synthesis of (±)-disparlure, the pheromone of the gypsy moth, in 49% overall yield via 6 steps.

• 公益社団法人 日本化学会の論文

著者

• Tsuboi Sadao

  Department Of Applied Chemistry Faculty Of Engineering Okayama University

• Sato Sadao

  Analytical And Metabolic Research Laboratories Sankyo Co. Ltd.

• Furutani Hiroyuki

  Department Of Synthetic Chemistry School Of Engineering Okayama University

• Kawazoe Kayoko

  Analytical and Metabolic Research Laboratories, Sankyo Co. Ltd.

• Takeda Akira

  Department of Applied Chemistry, Faculty of Engineering, Okayama University

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