Preparation and Utilization of Chiral alpha-and beta-Hydroxyacetylenes

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Intending to obtain versatile chiral 2-cyclopentenol building blocks, enzymatic resolution of several 2-substituted 2-cyclopentenol derivatives has been investigated. Having been tested, 2-carbethoxy-2-cyclopentenol has been cleanly resolved by lipase PS under both trans-esterification in organic solvent and deacylation in buffer solution in virtually complete enantiospecific manner in high chemical yields. Owing to characteristic feature of the enzymatic reaction, the reaction occurred at the same stereogenic configuraion which made enantiocomplementary resolution possible.Utilizing the optically pure cyclopentenols thus obtained, efficient syntheses of the key intermediate of 1,25-dihydroxyvitamin D_3 and vincamine have been achieved.