1992 Fiscal Year Final Research Report Summary

Preparation and Utilization of Chiral alpha-and beta-Hydroxyacetylenes

Research Project

Project/Area Number	02670941
Research Category	Grant-in-Aid for General Scientific Research (C)
Allocation Type	Single-year Grants
Research Field	Chemical pharmacy
Research Institution	TOHOKU UNIVERSITY
Principal Investigator	TAKAHASHI Michiyasu Tohoku University Pharmaceutical Institute Technical Official of Ministry of Education, 薬学部, 教務職員 (80089789)
Project Period (FY)	1990 – 1992
Keywords	enantiocontrolled synthesis / resolution / enantiocomplementary resolution / lipase / lipase in organic solvent / chiral synthon / vitamin D_3 / vincamine
Research Abstract	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.