申请人:Washington State University Research Foundation
公开号:US05817882A1
公开(公告)日:1998-10-06
Serricornin, the attractant pheromone of the cigarette beetle, is synthesized in high enantiomeric and diastereomeric purity via a series of reactions of asymmetric 2-(1-haloalkyl)-1,3,2-dioxaborolanes with Grignard reagents, which lead to the key intermediate \x9b,S-(R*,R*,R*)!-2-ethyl-3,5-dimethyl-l-octen-6-ol. Oxidative cleavage of the carbon-carbon double bond of \x9bS-(R*,R*,R*)!-2-ethyl-3,5-dimethyl-l-octen -6-ol with osmium tetroxide and sodium periodate yields serricornin.
烟草甲虫的引诱信息素Serricornin,通过不对称的2-(1-卤代烷基)-1,3,2-二氧杂环丁烷与Grignard试剂的一系列反应,合成出高对映体和对映异构体纯度的关键中间体\x9b,S-(R*,R*,R*)!-2-乙基-3,5-二甲基-1-辛烯-6-醇。将\x9bS-(R*,R*,R*)!-2-乙基-3,5-二甲基-1-辛烯-6-醇的碳-碳双键氧化裂解,使用高锰酸钾和碘酸钠得到Serricornin。