Molecular Desing and Synthesis of New Bioactive Substances

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The six independent subjects have been examined for past two research years and the successful resultes we obtained are summarized as follows.1. The new and versatile synnthetic procedure for alpha- (E&Z) -alkenylkentones by emplying alkenyllead reagents has been extended to the preparation of alpha-alkynylketones. An applikation of this technique to the synthesis of 13,14-didehydroisocarbacycline has been used successuflly.2. In order to clarify an affinity power of prostacycline analogues with a PGI_2 reseptor, an unexpectedly low potency of the analogues, 6-Isocarbacycline was reexamined. The analogue was successfully synthesized in the opteically active form.3. A strong inducer of thrombomoduline would be a candidate for new antithrombotic agent. As 9-cis-Retionic acid has more potent activity than its trans isomer, several 9-cis-analogues fixed with cycloalkanes and heterocycles have been syntesized. The analogues with 5-membered rings exhibit an activity equivanlent to 9-cis-Retinoic acid.4. In order to establish an efficient and versatile glycosylation reaction, a conceptionally different glycosylation based on decarboxylative glycosylation was investigate and the procedure gave good results in good yields and selectivity.5. Orthoesters formed from 1-dehydrosugar and another sugar shoul be good resourses for glycosyl bond formation. Reductive cleavage of one of a C-O bond would afford the corresponding glycoside. An investigation gave an excellent result.6. Stereochemically difined polyhydroxylated-cyclohexanones should be one of the most powerful syntheticintermediates for bioactive substances. Efficient and practical procedures for the ring-transformation from sugars to polyhydroxylated cyclohexanones were investigated and it wa established that the reactions proceed smoothly by using a catalytic amount of PdCl_2。