Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5285887 | Tetrahedron Letters | 2008 | 4 Pages |
Abstract
Lipase-catalyzed asymmetric acetylation of a mixture of (6R,1â²S,4â²S,5â²R)- and (6R,1â²R,4â²R,5â²S)-7â²-norsesquisabinen-4â²-ol (3) afforded a separable mixture of the recovered former and the acetate of the latter. The recovered alcohol was oxidized to (6R,1â²S,5â²R)-sesquisabina ketone (2), whose absolute configuration could be assigned by its CD comparison with (1R,5S)-sabina ketone (4). Conversion of (6R,1â²S,5â²R)-sesquisabina ketone (2) to the bioactive pheromone revealed the stereostructure of the male aggregation pheromone of the stink bug Erysarcoris lewisi (Distant) to be (2Z,6R,1â²S,5â²S)-2-methyl-6-(4â²-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol (sesquisabinen-1-ol, 1).
Related Topics
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Authors
Kenji Mori, Takuya Tashiro, Tomoko Yoshimura, Masami Takita, Jun Tabata, Shyuntaro Hiradate, Hajime Sugie,