摘要
以樟脑衍生物(-)-莰烷磺内酰胺为原料,经N-(E-2-烷烯酰基)莰烷-10,2-磺内酰胺与烷基格氏试剂的不对称Michael加成反应,LiAlH4还原断裂,3-甲基己醇的碘代反应及有机镉试剂与丙酰氯的偶联反应制得(R)-和(S)-石蚕蛾雄性性信息素6-甲基-3-壬酮,其光学纯度达96%ee以上.
(R)- and (S)-6-methyl-3-nananones,the sex pheromone produced by female caddisfly (Heseperophylax Occidentalis) were synthesized from R-camphor derivative-bornane-10,2-sultam via asymmetric Michael addition reaction of N-(E-2-enoyl)bornane-10,2-sultam with an alkyl magnesium reagent, reductive cleavage with LiAlH4, iodination of 3-methyl-1-hexanol and reaction of dialkyl cadmium with propionyl chloride. The enantiomeric excess of the total synthesis was over 96% ee.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2001年第6期463-466,共4页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金
