Abstract
An efficient (12 steps, 12% overallyield) and stereoselective total synthesis of (±)-serricornine (1) the sex pheromone of the cigarette beetle (Lasioderma serricornine F) is described. The preparation of intermediate 5, which encompasses the proper relative configuration of three contiguous chiral centers of (±)-invictolide, (3), is discussed.
total synthesis; (±)-serricornine; (±)-invictolide; pheromones
Stereoselective total synthesis of some insect pheromones: (±)-serricornine and (±)-invictolide
R. A. Pilli1
M. M. Murta1
Universidade Estadual de Campinas, Instituto de Química, Campinas, Brasil
An efficient (12 steps, 12% overallyield) and stereoselective total synthesis of (±)-serricornine (1) the sex pheromone of the cigarette beetle (Lasioderma serricornine F) is described. The preparation of intermediate 5, which encompasses the proper relative configuration of three contiguous chiral centers of (±)-invictolide, (3), is discussed.
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Publication Dates
-
Publication in this collection
24 June 2009 -
Date of issue
1991
