Asymmetric syntheses of bioactive compounds possessing inhibition activity of cell adhesion and antitumour activity

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In this scientific program, asymmetric syntheses of bioactive compounds possessing inhbition activity of cell-adhesion and antitumour activity were carried out based on enzymatic function.1. Total synthesis of macrosphelide A possessing inhibition activity of cell-adhesion was achieved based on enzymatic function. The key chiral intermediate, methyl (4R,5S)-5-acetoxy-4-benzyloxy-(2E)-hexenoate was obtained by the enantioselective hydrolysis using lipase of the corresponding racemate.2. Total synthesis of (-)-chuangxinmycin having antimicrobial activity was achieved based on the reaction of 4-iodoindole and methyl (2R,3S)-epoxy butanoate. This chiral intermediate was also obtained based on the enantioselective hydrolysis using lipase of the racemic (2,3)-trans-2-acetoxy-3-chloro butanoate.3. The synthesis of decalin type chiral synthon possessing decahydro-5,5,8a-trimethyl-naphthalene skeleton was achieved based on enzymatic function. Thus obtained chiral synthons were converted into (-)-ambrox bearing a powerful amber-type aroma and marine natural product, (+)-zonarol.4. Asymmetric syntheses of peptidyl nucleoside antibiotic, nikkomycin B and vitamin E were also achieved based on enzymatic function.