53(P15) リパーゼによる構造異性体の分離を基盤とした(-)-Anisomycin,(+)-Elvirolの合成(ポスター発表の部)

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概要

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• The most common utilization of lipase is enantioselective resolution and good results were obtained in organic solvent or aqueous buffer solution. Recently lipase has been applied to regioselective esterification of alcohol having both primary and secondary hydroxyl groups. In this work separation of structural isomers by lipase Amano P (Pseudomonas sp.) and their application to the synthesis of natural product are described in two sets of experiment. The first case which is a separation of two optically active 5-acetoxy-4-arylpentenoates, (4R)-1 and (4R)-2, gave 4-(4'-methoxyphenyl)-(2E)-pentenoate ((4R)-3) and unchanged (4R)-2. The former (4R)-3 was effectively derived to antibiotic (-)-anisomycin. The stereoselective conversion of (4R)-5-hydroxy-4-(4' -methoxyphenyl)-(2E)-pentenoate (3) into the (4S)-4-hydroxy-5-(4'-methoxy-phenyl)-(2E)-pentenoate (7) using AgNO_3/MS 4A/MeNO_2 system was accomplished along with complete inversion at the C_4-position and the synthesis of the intermediate (4S)-(-)-16 for the chiral synthesis of (-)-anisomycin from (4S)-7 based on osmium tetroxide-catalyzed stereoselective hydroxylation was achieved. In the second case, a separation of mixture of optically active 4-arylpentenoate (4S)-4 and 2-arylpentenoate (2R)-5 was carried out to afford (2R)-2-aryl-5-hydroxypentenoate and unchanged (4S)-4 and (4S)-4 was applied for the first chiral synthesis of (+)-elvirol. Hydrolysis of (4S)-4 followed by the successive conversion gave (+)-elvirol which is sesquiterpenoid isolated from Elvira biflora DC.

• 天然有機化合物討論会の論文
• 1999-09-01

著者

• 尾能 満智子

  東邦大薬

• 秋田 弘幸

  東邦大薬

• 尾能 満智子

  School Of Pharmaceutical Sciences Toho University

• 鈴木 計子

  東邦大薬

• 秋田 弘幸

  東邦大学薬学部

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