Nakanishi Akira, Mori Kenji
Department of Applied Biological Chemistry, The University of Tokyo, Tokyo.
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。
