Synthesis of Optically Active Forms of Some Useful Bioactive Substanus

以光学活性形式合成了各种生物活性物质。在信息素的情况下，进行了广泛的工作，这将是在IUPAC大会（1989年，瑞典）作为特邀演讲。(1)以下信息素合成为纯的对映异构体：serricornin、endo-brevicomin、14-甲基-1-十八烯、stegobinone、stegobiol、invictolide、家鼠信息素、pityol、grandisol、1-甲基-2-环己烯-1-醇、四氢-2，2，6-三甲基-2H吡喃-3-醇、-multistriatin和sitophilure。这些信息素对映体被提供给生物学家。(2)制备保幼激素I、II和III的天然存在的对映体。还制备了保幼激素III的非天然对映体，发现其活性远低于天然对映体（1/5240）。(3)以光学活性形式合成了以下抗生素：子囊二氢菌素、子囊呋喃酮、唑那洛尔、塔拉霉素A和B、并环戊烯内酯E和阿司他丁A。(4)所有可能的立体异构体的hernandulcin，天然存在的甜味剂，被合成，只有天然的一个被发现是甜的。同时还合成了甜苷白云苷的苷元。合成了米扎菌素A、B和C的对映体。天然的对映体是有效的植物抗毒素。(6)制备了蓼二醛的对映体，发现两者都具有昆虫拒食活性。

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.