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Name Nakamura Hiroshi
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Title

Formal total synthesis of (+)-macrosphelide A based on regioselective hydrolysis using lipase 

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Summary

Three kinds of seco-macrosphelide A congeners, were chem. synthesized, and exposed to the lipase OF-360 from Candida rugosa to give three hydroxy carboxylic acids.  Macrolactonization of the corresponding precursor hydroxy acid gave 12-membered lactone I in 47% overall yield, while that of the seco-acid II afforded (-)-dibenzyl macrosphelide A in 27% overall yield.  Macrolactonization of the hydrolysis product, seco-acid III, provided (-)-dibenzyl macrosphelide A (5% overall yield) and 12-membered lactone I (20% overall yield) concurrently.
(2002), 50(5),692-696

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Chemical & Pharmaceutical Bulletin

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2002/05

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International Journal

 

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