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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. shu

The Stereoselective Synthesis of Tobacco Beetle Pheromone-(7S)-(-)-4,6-dimethyl-7-hydroxyl-3-nonanone

1.
Department of Applied Chemistry, Yunnan University, Kunming 650091

Received Date: 15 September 2000
Available Online: 6 February 2001
Fund Project: 国家自然科学基金(29762006) (29762006)

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%.
- tobacco beetle pheromone,
- serricornin,
- stereoselective synthesis
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