(R)和(S)-4-甲基-1-壬醇的合成研究

（R）和（S）－4－甲基－1－壬醇是黄粉虫（Tenebrio molitorL.）雌性性引诱信息素，以天然樟脑衍生物莰烷－10，2－磺内酰胺为原料，在有或无Cul催化条件下以巴豆酰基鞭莰烷－10，2－磺内酰胺的不对称Michael加成反应为关键步骤对该信息素进行了合成，其加成产物（3 ′R）和（3′S）－N－3′－甲基辛酰基莰烷－10，2－磺内酰胺以LiAlH4^-还原断裂及HBr溴化反应后，再经3－甲基辛基溴化镁与甲醛反应即合成出目标产物（R）和（S）－4－甲基－1－壬醇，全合成总产率可42％，目标产物对映异构体纯度可达96％e,e此合成法具有步骤短、产率高及手性助剂可回收利用等优点。

Study on synthesis of (R) and (S)-4-methyl-1-nonanol

R) and (S) -4-methyl-1-nonanol, the sex attractant of the yellow mealworn (Tenebrio molitor L.), were synthesized from R -camphor derivative bornane-10,2-sultam via asymmertic michael addition of N-crotonoylbornane-10,2-sultam in the presence of CuI or no CuI as key step. The additive products (3R) and ( 3S -N-3-methyloctanoylborane-10,2-sultam were reductive cleaved with LiAlH 4 and brominated with HBr, then reaction of 3-methyloctylmagnesium bromide with formaldehyde gave the target products (R) and (S) -4-methy-1-nonanol, the yield of the total synthesis is over 42?% and the enantiomeric excess of the target products is over 96?%e.e. The method has advantages of short routes, high yield and reusability of chiral auxiliary.