文章基本信息

标题：Absolute Configuration of Cecropia Juvenile Hormone
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作者：Andre S. Meyer ; Edith Hanzmann ; Robert C. Murphy 等
期刊名称：Proceedings of the National Academy of Sciences
印刷版ISSN：0027-8424
电子版ISSN：1091-6490
出版年度：1971
卷号：68
期号：9
页码：2312-2315
DOI：10.1073/pnas.68.9.2312
语种：English
出版社：The National Academy of Sciences of the United States of America
摘要：The absolute configuration of the predominant Cecropia hormone, methyl 12,14-dihomojuvenate, has been determined to be methyl (E,E)-(10R,11S)-(+)-10,11-epoxy-7-ethyl-3,11-dimethyl-2, 6-tridecadienoate (I). The less abundant hormone, methyl 12-homojuvenate, can be presumed by analogy to have the corresponding 3,7,11-trimethyldienoate structure (II). The assignment has been established with microamounts of substance by applying Horeau's method to the glycol derivative (III) of the hormone. The course of the perchloric acid-catalyzed epoxide ring opening of I was checked by conducting the conversion in 18O-labeled water. It has been ascertained that the configuration at the secondary hydroxyl group of the resulting III remained unchanged. On the other hand, the hydration proceeded with a surprisingly high rate of cis opening.
关键词：Horeau's method ; glycol ; epoxide hydration ; PMR ; mass spectroscopy