Synthesis of Optically Active Forms of Some Useful Bioactive Substanus

以光活性形式合成了各种生物活性物质。在信息素方面，进行了广泛的工作，并将作为邀请演讲在IUPAC大会上发表（1989年，瑞典）。(1)以纯对映体的形式合成了下列信息素：丝光鸡毛苷、内芽草素、14-甲基-1-十八烯、剑哥宾酮、剑哥生物醇、invictolide、家鼠信息素、pityol、grandiol、1-甲基-2-环己烯-1-醇、四氢-2,2,6-三甲基- 2h吡喃-3-醇、-multistriatin、sitophilure。这些信息素对映体提供给生物学家。(2)制备了天然存在的幼激素I、II和III对映体。还制备了幼激素III的非天然对映体，发现其活性远低于天然对映体（1/5240）。(3)合成了抗坏血氯、抗坏血呋喃酮、唑诺罗、他霉素A和他霉素B、戊烯内酯E和曲古霉素A。(4)合成了天然甜味剂hernandulcin的所有可能的立体异构体，发现只有天然甜味剂hernandulcin是甜的。同时合成了甜苷白菊花苷的苷元。合成了稻谷毒素A、B和C的对映体。天然对映体是有效的植物抗菌素。(6)制备了多聚体的对映体，发现两者都具有抗虫活性。

Various bioactive substances were synthesized in optically active forms. In the cace of pheromone, extensive work was executed which will be delivered as an Invited Lecture at IUPAC Congress (1989, Sweden). (1) The following pheromones were synthesized as pure enantiomer(s): serricornin, endo-brevicomin, 14-methyl-1-octadecene, stegobinone, stegobiol, invictolide, house mouse pheromone, pityol, grandisol, 1-methyl-2-cyclohexen-1-ol, tetrahydro-2,2,6-trimethyl-2H pyran-3-ol, -multistriatin, and sitophilure. These pheromone enantiomers were supplied to biologists. (2) Naturally occurring enantiomers of juvenile hormone I, II, and III were prepared. Unnatural enantiomer of juvenile hormone III was also prepared and found to be far less active (1/5240) than the natural enantiomer. (3) The following antibiotics were synthesized in optically active forms: ascochlorin, ascofuranone, zonarol, talaromycin A and B, pentalenolactone E, and trichostatin A. (4) All of the possible stereoisomers of hernandulcin, the naturally occurring sweetner, were synthesized, and only the natural one was found to be sweet. The aglycone of the sweet glycoside baiyunoside was also synthesized. The enantiomers of oryzalexins A, B, and C were synthesized. The natural enantiomers were potent as phytoalexins. (6) The enantiomers of polygodial were prepared, and both were found to be active as an insect antifeedant.