Formal Total Synthesis of (+)-Macrosphelide A Based on Regioselective Hydrolysis Using Lipase

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概要

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• 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

• NAKAMURA Hiroshi

  School of Dentistry, Aichi-Gakuin University

• Honda Naoko

  School Of Pharmaceutical Sciences Toho University

• Akita Hiroyuki

  School Of Parmaceutical Sciences Toho University

• Ono Machiko

  School Of Pharmaceutical Sciences Toho University

• ARAKAWA Satoko

  School of Pharmaceutical Sciences, Toho University

• Arakawa Satoko

  School Of Pharmaceutical Sciences Toho University

• Ono Machiko

  School Of Pharmaceutical Sciences International Univ. Of Health And Welfare

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