83 キラルシクロブタノンの新規合成法の開発 : 数種の昆虫フェロモンおよびセスキテルペンの不斉合成への展開(ポスター発表の部)
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概要
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1. A Novel Approach to Chiral Cyclobutanones Using Chiral 1,3-Oxathiane as Chiral Auxiliary Chiral aldehyde(7) was synthesized through cyclobutanone(5), which was in turn derived by concerted stereospecific ring enlargement of cyclopropyl alcohol (3) and (4) followed by base catalyzed epimerization of (6). The compound(7) was converted into pheromone, R-(+)-dodecan-5-olide(9) and (R)-(+)-5-[(Z)-dec-1-enyl] dihydrofuran-2(3H)-one(13). Chiral cyclobutanone alcohol(16), which was prepared by concerted 1,2-rearrangement of cyclopropyl alcohol(15), was also converted into pheromone, (-)-frontalin(21) via γ-butyrolactone(17). 2. A Novel Approach to Chiral Cyclobutanones by Tandem Asymmetric Epoxidation and Enantiospecific Ring Expansion of Cyclopropylidene Alcohols. A tandem asymmetric epoxidation and enantiospecific ring expansion of 2-cyclopropylideneethanols(22) via chiral oxaspiropentanes(23) afforded chiral 1-alkyl- or 1-aryl-1-hydroxymethylcyclobutanones(24) in high yields and high enantiomeric excess. Chiral cyclobutanones(29) and its enantiomer thus prepared, were converted into (+)-α-cuparenone and (-)-α-cuparenone via (30) and its enantiomer. Enantioselective total synthesis of (+)-laurene(41) was also achieved starting from chiral cyclobutanone(30) via cyclopentanone(35), cyclopentanol (39), and cyclopentanone(40). The formal total synthesis of sex specific compound(47) and the potential intermediate(51) of its enantiomer(52) was also achieved via tandem asymmetric epoxidation and enantiospecific ring expansion of cyclopropylidene alcohol(42) as key step.
- 1992-09-10
著者
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福本 圭一郎
東北大
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福本 圭一郎
東北大・薬
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永持 雅敏
東北大・薬
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石橋 大樹
東北大・薬
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根本 英雄
東北大薬
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福本 圭一郎
東北大薬
-
永持 雅敏
東北大薬
-
石橋 大樹
東北大薬
-
山田 敏江
東北大薬
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