引用本文:
古昆, 李鲜, 陈静波, 刘复初, 林军. 烟草甲虫性信息素(7S)-(-)-4,6-二甲基-7-羟基-3-壬酮的立体选择性合成[J]. 应用化学,
2001, 18(8): 662-663.
Citation: GU Kun, LI Xian, CHEN Jing-Bo, LIU Fu-Chu, LIN Jun. The Stereoselective Synthesis of Tobacco Beetle Pheromone-(7S)-(-)-4,6-dimethyl-7-hydroxyl-3-nonanone[J]. Chinese Journal of Applied Chemistry, 2001, 18(8): 662-663.
Citation: GU Kun, LI Xian, CHEN Jing-Bo, LIU Fu-Chu, LIN Jun. The Stereoselective Synthesis of Tobacco Beetle Pheromone-(7S)-(-)-4,6-dimethyl-7-hydroxyl-3-nonanone[J]. Chinese Journal of Applied Chemistry, 2001, 18(8): 662-663.
烟草甲虫性信息素(7S)-(-)-4,6-二甲基-7-羟基-3-壬酮的立体选择性合成
English
The Stereoselective Synthesis of Tobacco Beetle Pheromone-(7S)-(-)-4,6-dimethyl-7-hydroxyl-3-nonanone
Abstract:
Using an available compound 3-pentanone(1) as starting material, the key intermediate compound 4,6-dimethyl-3,7-nonandione(5) was synthesized through the additionelimination of silylenol ether and Michael addition of T-methylene 3-pentanone(4) with silylenol ether(2). In the presence of chiral reagent 6U-phenyl amino-3U,5T-chlorestandiol(7), compound (5) was reduced by KBH4 directly to give Tobacco Beetle Pheromone (7S)-(-)-4,6-dimethyl-7-hydroxyl-3-nonanone(6). [T]D25=-35.87°(c=0.23, CHCl3), overall yield 23.9%.
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Key words:
- tobacco beetle pheromone
- / serricornin
- / stereoselective synthesis
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