手性3,7-二甲基-5,6-二羟基-辛-7-烯醛中间体的合成

摘要

以天然长叶薄荷酮［R-（+）-Pulegone］为起始原料，经过一系列立体选择性化学反应步骤，成功地建立了3个手性中心，从而完成了具有抗艾滋病活性Didemnaketals 类似物的关键中间体3,7-二甲基-5,6-二羟基-辛-7-烯醛中间体的合成. 发现PCC与三级环氧醇8和9的非对映选择性反应，使得9被完全氧化，而8以93%的产率回收，其de值高达98%.%A stereoselective synthesis of (3S,5S,6S)-3,7-dimethyl-5,6-dihydroxy-7-en-octanal, a key intermediate, for the synthesis of the HIV-inhibitory didemnaketals analogue, was performed via a series of reactions from the natural(+)-pulegone. In this approach, an interesting and valuable diastereo-recognizable reaction between tertiary hydroxyepoxides and PCC was found. Therefore, the mixture of compounds 8 and 9 was treated with PCC to recover 8 in 93% yield and de 98% purity.