9,10-环氧-3,6-二十一碳二烯和9,10-环氧-1,3,6-二十一碳三烯的(3Z,6Z,9S,10R)-异构体的新合成方法，这两种物质是美国白蛾雌蛾的性信息素成分。
New synthesis of the (3Z,6Z,9S,10R)-isomers of 9,10-epoxy-3,6-henicosadiene and 9,10-epoxy-1,3,6-henicosatriene, pheromone components of the female fall webworm moth, Hyphantria cunea.
作者信息
Nakanishi Akira, Mori Kenji
机构信息
Department of Applied Biological Chemistry, The University of Tokyo, Tokyo.
出版信息
Biosci Biotechnol Biochem. 2005 May;69(5):1007-13. doi: 10.1271/bbb.69.1007.
(3Z,6Z,9S,10R)-9,10-Epoxy-3,6-henicosadiene (1) and (3Z,6Z,9S,10R)-9,10-epoxy-1,3,6-henicosatriene (5), pheromone components of the female fall webworm moth (Hyphantria cunea Drury), were synthesized by starting from (2S,3R)-2,3-epoxy-4-t-butyldimethylsilyloxy-1-butanol (8). Epoxide 8 was prepared by employing lipase-catalyzed asymmetric acetylation of (+/-)-8 as the key optical resolution step.
（3Z，6Z，9S，10R）-9，10-环氧-3，6-二十一碳二烯（1）和（3Z，6Z，9S，10R）-9，10-环氧-1，3，6-二十一碳三烯（5）是雌性美国白蛾（Hyphantria cunea Drury）的性信息素成分，它们以（2S，3R）-2，3-环氧-4-叔丁基二甲基硅氧基-1-丁醇（8）为起始原料合成。环氧化合物8的制备采用脂肪酶催化的（±）-8不对称乙酰化作为关键的光学拆分步骤。
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