Concise Syntheses of Coronarin A, Coronarin E, Austrochaparol and Pacovatinin A
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概要
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Total syntheses of (+)-coronarin A (1), (+)-coronarin E (2), (+)-austrochaparol (3) and (+)-pacovatinin A (4) were achieved from the synthetic (+)-albicanyl acetate (6). Dess-Martin oxidation of (+)-albicanol (5) derived from the chemoenzymatic product (6) gave an aldehyde (7), which was subjected to Julia one-pot olefination using β-furylmethyl-heteroaromatic sulfones (8 or 9 ) gave (+)-trans coronarin E (2) and (+)-cis coronarin E (12) with high cis-selectivity. The synthesis of (+)-coronarin A (1) from (+)-trans coronarin E (2) was achieved, while (+)-cis coronarin E (12) was converted to the natural products (+)-(5S,9S,10S)-15,16-epoxy-8(17),13(16),14-labdatriene (13) and (+)-austrochaparol (3). By the asymmetric synthesis of (+)-3, the absolute structure of (+)-3 was determined to be 5S, 7R, 9R, 10S configurations. Homologation of (+)-albicanol (5) followed by allylic oxidation gave (7α)-hydroxy nitrile (17), which was finally converted to the natural (+)-pacovatinin A (4) in 8 steps from (+)-albicanol (5).
- 2008-03-01
著者
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Fujii Mikio
Faculty Of Pharmaceutical Sciences Toho University
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Akita H
Toho Univ. Chiba Jpn
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Miyake Takahiro
School Of Pharmaceutical Sciences Toho University:tsukuba Research Institute Novartis Pharma K.k.
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Akita Hiroyuki
Faculty Of Pharmaceutical Sciences Toho University
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MIYAKE Takahiro
Faculty of Pharmaceutical Sciences, Toho University
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UDA Keisuke
Faculty of Pharmaceutical Sciences, Toho University
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KINOSHITA Masako
Faculty of Pharmaceutical Sciences, Toho University
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Uda Keisuke
Faculty Of Pharmaceutical Sciences Toho University
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Kinoshita Masako
Fac. Of Pharmaceutical Sciences Toho Univ.
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Fujii Mikio
Faculty of Engineering,Tokushima University
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