PURPOSE: To stereoselectively produce all stereoisomers of new 5-substituted S-lactone except one part of them useful as inhibitor of cholesterol biosynthesis, perfume or flavor, by using streptenol through new intermediate.
CONSTITUTION: The new compound of formulae II-III or its enantiomer is obtained by diastereoselecively reducing the compound of formula I or its enantiomer obtained by acetalization, oxidation, diastereoselective reduction and deacetalization process of the compound of formula I in this order. The compound of formulae IV-VII (the compound except formula IV (R1 is pentyl) is new one) is obtained by stereoselectively oxidizing the obtained these compounds. Otherwise, the new compound of formulae IV-VII (R1 is CH2OH) is obtained by allowing these compounds to react with the compound of the formula, R3-O (R3 is 1-5C alkyl or tertiary butyl), and then carrying out ketalization by acetone or dimethoxypropane, ozonization and oxidation of protecting group. In formula I, R1 is 3-15C alkyl or 3-15C alkenyl having 1-7 C-C = bonding.
ZUZANE GURAAPURAI
EANORUTO GURANTSUAA
IFUONE ROMAIKE
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