Abstract

Diastereoselective allylation of (R)-2,3-O-cyclohexylideneglyceraldehyde with 3-(bromomethyl)but-3-enoate, followed by reduction with zinc, gave homoallylic alcohol which was subjected to lactonization. Opening of the lactone ring in the latter afforded methyl (3S)-5,5-dimethoxy-3-methylpentanoate with a high yield and enantioselectivity. This compound is a valuable intermediate product in the synthesis of pheromone of the mealworm beetle Tenebrio molitor L., a pest of stored cereals.

中文翻译：

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黄粉虫黄粉虫信息素的合成

摘要

（R）-2，3- O-环己叉基甘油醛与3-（溴甲基）丁-3-烯酸酯的非对映选择性烯丙基化，然后用锌还原，得到均丙醇，将其内酯化。后者中的内酯环的打开提供了高产率和对映选择性的（3S）-5，5-二甲氧基-3-甲基戊酸甲酯。该化合物是粉虫甲虫Tenebrio molitor L.（一种储存谷物的害虫）的信息素合成中的一种有价值的中间产物。