Synthesis of Optically Active Forms of Some Useful Bioactive Substanus

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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.