Studies on structurally simple α,β-butenolides-I. New syntheses of racemic γ-hydroxymethyl-α,β-butenolide and derivatives

J. Cardellach, C. Estopa, J. Font, M. Moreno-Mañas, R. M. Ortuño, F. Sanchez-Ferrando, S. Valle, L. Vilamajo

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Abstract

Exhaustive approaches to the synthesis of racemic γ-heterosubstituted γ-methyl-α,β-butenolides are presented, starting mainly 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. © 1982.
Original languageEnglish
Pages (from-to)2377-2394
JournalTetrahedron
Volume38
Issue number15
DOIs
Publication statusPublished - 1 Jan 1982

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