STUDIES ON STRUCTURALLY SIMPLE α,β-BUTENOLIDES-I NEW SYNTHESIS OF RACEMIC γ-HYDROXYMETHYL-α,β-BUTENOLIDE AND DERIVATIVES

Article abstract of DOI:10.1016/0040-4020(82)87016-6

Exhaustive approaches to the synthesis of racemic γ-heterosubstituted γ-methyl-α,β-butenolides are presented, starting from C3 synthons (glyceraldehyde, glycidaldehyde, acrolein and 2,3-epoxypropyl ethers).Good general methods for the preparation of γ-hydroxymethyl-α,β-butenolide 2, several of its ether derivatives, as well as of γ-bromomethyl-α,β-butenolide 5, are given.The reactivities of these structurally simple but highly functionalized compounds, convenient synthons for more complex molecules, are preliminarily explored.