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Paper | Special issue | Vol 67, No. 2, 2006, pp.705-720
Published online, 27th September, 2005
DOI: 10.3987/COM-05-S(T)67
A Versatile Stereoselective Approach to Paraconic Acids

Marta Amador, Xavier Ariza,* and Jordi Garcia*

*Department of Organic Chemistry, University of Barcelona, Av. Diagonal 647, 08028 Barcelona, Spain

Abstract

A versatile methodology has been developed for the independent stereochemical control in the construction of all the stereocenters of the γ-butyrolactone skeleton that are present in paraconic acids (1 and 2). The configuration of the γ-carbon came from an enantiopure alk-2-yne-1,4-diol. Stereoselective partial reduction to a (Z)- or (E)-alk-2-ene-1,4-diol (10) controlled the stereochemistry of the β-carbon whereas the α-carbon stereochemistry in 1 was partially selected by a (Z)- or (E)-enolate formation of the 1,4-dipropanoate derived from diol (10).