| Research Abstract |
1. Systematic Synthesis of Biologically Active Iridoids.
(1) Synthesis of Penstemide and Didrovaltrate. Optically active penstemide and didrovaltrate were synthesized very efficiently starting from (+)-genipin by the sequence of functional group transformations. (2) Synthesis of Allamandicin and Plumericin. We have accomplished the synthesis of optically active allamandicin and plumericin starting from (+)-genipin. (3) Synthesis of Seco-iridoids. Seco-loganin, sweroside, kingiside, morronoside, gentiopicroside and sarracenin were synthesized efficiently starting from (+)-genipin. (4) Synthesis of Petiodial. (+)-Pctiodial was synthesized from (+)-genipin. The absolute structure of natural petiodial was determined by this synthesis. (5) Synthesis of Nepetalactol and Neomatatabiol. Nepetalactol, sex attractant for aphid, and neomatatabiol, attractant for lace wing were synthesized from (+)-genipin. (6) Synthesis of (+)-Tecomanin. Tecomanin, monoterpene alkaloid was synthesized from (+)-genipin.
2. Synthesis of (<plus-minus>)-Jolkinolide A, B, and E. Jolkinolide A, B, and E were efficiently synthesized from 9-methoxycarbony1-4, 4, 10-trimethyl-DELTA^6-8-octalone through podocalpenone. A new synthetic method of gamma-ylidenbutenolid consisting of mild esterification and succeeding intramolecular Wittig-Horner reaction of alpha-diketone was developed.
3. Development of new synthetic reactions. (1). Stereoselective synthesis of substituted 2-methoxy-1, 3-butadienes was developed. (2). New synthetic method of cyclic peroxide consisting of formal [2+2+2] cycloaddition of molecular oxygen, 1, 3-diketone, and olefin was developed. (3). New synthetic reactions utilizing electrochemical oxidation of silicon-substituted heteroatom compounds were developed.
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