| Project/Area Number |
02670941
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | TOHOKU UNIVERSITY |
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Principal Investigator |
TAKAHASHI Michiyasu Tohoku University Pharmaceutical Institute Technical Official of Ministry of Education, 薬学部, 教務職員 (80089789)
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| Project Period (FY) |
1990 – 1992
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| Project Status |
Completed (Fiscal Year 1992)
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| Budget Amount *help |
¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 1992: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1991: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1990: ¥900,000 (Direct Cost: ¥900,000)
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| Keywords | enantiocontrolled synthesis / resolution / enantiocomplementary resolution / lipase / lipase in organic solvent / chiral synthon / vitamin D_3 / vincamine / キラル2-メチル-2-シクロペンテノール / キラル2-カルボエトキシ-2-シクロペンテノール / リパーゼ関与不斉分割 / 不斉加水分解 / エナンチオ相補分割法 / キラル合成ブロック / 2ーメチルー2ーシクロペンテノ-ル / ジシクロペンタジエノ-ル / 2ーカルボエトキシー2ーシクロペンテノ-ル / アファノリフィン / ノルベンゾモルファン / 活性型ビタミンD_3 / キラルシクロペンテノ-ル / リパ-ゼ / ヒルステン / ジシクロペンタジェン / アファノルフィン / [2,3]ーウィティッヒ転位 / モッシャ-法 |
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| 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.
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