天蚕蛾保幼激素的短程立体选择性合成。
A short stereoselective synthesis of cecropia juvenile hormone.
作者信息
Loew P, Siddall J B, Spain V L, Werthemann L
出版信息
Proc Natl Acad Sci U S A. 1970 Nov;67(3):1462-4. doi: 10.1073/pnas.67.3.1462.
A very short synthesis of the racemic cecropia hormone has been realized, utilizing a Claisen reaction. Methyl 6-hydroxy-3-methyl-7-methylene-2-trans-nonenoate, on treatment with the dimethyl ketal of 3-chloro-3-methyl-2-pentanone and a catalytic amount of 2,4-dinitrophenol, is transformed directly into methyl 11-chloro-3,11-dimethyl-7-ethyl-10-oxo-2-trans, 6-trans-tridecadienoate. Selective reduction gives a mixture of diastereoisomeric chlorohydrins separable by chromatography. The predominant threo-chlorohydrin is transformed into the juvenile hormone.
利用克莱森反应实现了外消旋天蚕激素的非常简短的合成。6-羟基-3-甲基-7-亚甲基-2-反式壬烯酸甲酯在与3-氯-3-甲基-2-戊酮的二甲基缩酮及催化量的2,4-二硝基苯酚反应时，直接转化为11-氯-3,11-二甲基-7-乙基-10-氧代-2-反式,6-反式-十三碳二烯酸甲酯。选择性还原得到可通过色谱法分离的非对映异构氯醇混合物。主要的苏式氯醇被转化为保幼激素。
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