Formal Total Synthesis of (+)-Macrosphelide A Based on Regioselective Hydrolysis Using Lipase
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概要
- 論文の詳細を見る
Three kinds of seco-macrosphelide A congeners, (4R,5S,1OR,11S,15S)-6, (4R,5S,9S,14R,15S)-7 and (3S,8R,9S,14R,15S)-8 were chemically synthesized, and they were exposed to the lipase OF-360 from Candida rugosa to give three hydroxy carboxylic acids, respectively. Macrolactonization of the hydroxy acid (4R,5S,1OR,11S)-18 derived from (4R,5S,10R,11S,15S)-6 gave 12-membered lactone (19) in 47% overall yield from 6, while that of the seco-acid (4) derived from (4R,5S,9S,14R,15S)-7 afforded (-)-dibenzyl macrosphelide A (25) in 27% overall yield from 7. Macrolactonization of the hydrolysis product, seco-acid (5) derived from (3S,8R,9S,14R,15S)-8, provided (-)-dibenzyl macrosphelide A (25) (5% overall yield from 8) and 12-membered lactone (19) (20% overall yield from 8) concurrently.
- 公益社団法人日本薬学会の論文
- 2002-05-01
著者
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NAKAMURA Hiroshi
School of Dentistry, Aichi-Gakuin University
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Honda Naoko
School Of Pharmaceutical Sciences Toho University
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Akita Hiroyuki
School Of Parmaceutical Sciences Toho University
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Ono Machiko
School Of Pharmaceutical Sciences Toho University
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ARAKAWA Satoko
School of Pharmaceutical Sciences, Toho University
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Arakawa Satoko
School Of Pharmaceutical Sciences Toho University
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Ono Machiko
School Of Pharmaceutical Sciences International Univ. Of Health And Welfare
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