Synthesis of Cyclopentane-Macrolides Based on Lewis Acid Mediated Cyclization of Chiral Epoxy-Alcohols
| Project/Area Number |
01571137
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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 |
YATAKEYAMA Susumi Tohoku University Pharmaceutical Institute Research ASsociate, 薬学部, 助手 (20143000)
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| Project Period (FY) |
1989 – 1991
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| Project Status |
Completed (Fiscal Year 1991)
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| Budget Amount *help |
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1991: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1990: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1989: ¥900,000 (Direct Cost: ¥900,000)
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| Keywords | Sharpless asymmetric epoxidation / Lewis acid mediated cyclization / Substituted cyclopentane / Enantiocontrolled synthesis / Brefeldin A / Brefeldin C / Macrolide antibiotic / Chiral epoxy-alcohol / アリルシラン / 抗生物質 / マクロリド / キラル置換シクロペンタン / Hybridialactone / Ecklonialactone A / (R,R)ー3,4ージヒドロキシメチルシクロペンテン / ルイス酸触媒下の環化 / ブレフェルディンA / キラル合成 / キラルシクロペンタン / ブレフェルディンC |
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| Research Abstract |
In the course of investigation concerning intramolecular Lewis acid mediated nucleophilic opening of epoxy-alcohols, we have developed an enantioselective route to a substituted cyclopentane 2 from an allyl alcohol 1 through four manipulations ; i)Sharpless asymmetric epoxidation, ii)Lewis acid mediated cyclization ; iii)protection as acetonide ; iv)ozonolysis followed by base-catalyzed epimerization. The generality of this method was proved by the fact that regardless of the stereo- and regio-chemistry of pre-exsisting substituents(R^1 and/or R^2)of 1, tri- or four-substituted cyclopentanes 2 with 1, 2-trans configuration were obtained in high enantiomeric excess(>90% ee). The synthetic utility of this method was demonstrated by the achievement of enantiocontrolled syntheses of(+)-brefeldin A(3)and(+)-brefeldin C(4)from 2(R^1=H, R^2=OBn or R^1=R^2=H).
brefeldin C(4)from 2(R'=H, R2=OBn or RI=R2=H).
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Report
(4 results)
Research Products
(6 results)
