Volume 24, Issue 32
Preparative Organic Chemistry
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ChemInform Abstract: Preparation of Lactones with Several Ring Sizes via the Same Intermediate.

S. ROBIN

S. ROBIN

Lab. Carbocycles, Ass. CNRS, Univ. Paris-Sud, 91405 Orsay, Fr.

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F. HUET

F. HUET

Lab. Carbocycles, Ass. CNRS, Univ. Paris-Sud, 91405 Orsay, Fr.

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First published: August 10, 1993

Abstract

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ChemInform Abstract

The chiral siloxybutyl sulfone (S)-(I) is subjected to substitution reactions to give derivatives bearing an ester or acetal moiety. These undergo desilylation and cyclization to form a lactone (IV) or lactols (IX), (XIII). The latter are converted to the lactones (X) and (XIV) respectively. The reductive desulfonation of (IV) and the elimination of sulfinic acid from (X) are also described.

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