Efficient Desymmetrization of 'Pseudo'-C[sub 2]-Symmetric Substrates: Illustration in the Synthesis of a Disubstituted Butenolide from Arabitol.

A short synthesis of the homochiral disubstituted butenolide 1 is described in four steps from arabitol. The key steps are the selective kinetic protection of arabitol and the cyclization of 11 to form the butenolide ring. This last transformation represents a rare example of a fully stereoselective cyclitive desymmetrization process of a "pseudo"-C[sub 2]-symmetric substrate. [ABSTRACT FROM AUTHOR]