Development and Utilization of Versatile Chirl Building Blocks

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During the present investigation, three versatole chiral building blocks exhibiting convex-face selectivity have been developed by employing either enzymatic or chemical kinetic resolution method. All building blocks possess an enone and a masked enone moieties which allowed diastereocontrolled modification owing to their inherent stereochemical nature. Versatility of these chiral molecules as chiral building blocks were demonstrated by enantio- and diastereocontrolled construction of a variety of physiologically active natural products synthesized in the present investigation are prostaglandins (key intermediate), (-)-morphine, (+)-tanikolide, (-)-malyngolide, (-)-kainic acid, (+)-febrifugine, (+)- and (-)-levoglucosenone, (-)-shikimic acid, (-)-semburine, (-)-antirhine, (-)-quinine (key intermediate), (+)-uleine, (-)-aristeromycin, (+)-arnicenone, (-)-physostigmine, (-)-physovenine, (-)-aphanorphine, (-)-iridolactone, (+)-pedicularis-lactone, simplactone A, (-)-tetrahydrolipstatin, eight aldohexoses, six conduritols, pseudomonic acids, ferruginol, (+)-20R-dihydrocleavamine, (-)-quebrachamine, (-)-menisdaurilide, (-)-mesembrine, and (+)-sceletinum A.