ChemInform Abstract: An Efficient Synthesis of (S)‐5‐Hydroxymethyl‐2(5H)‐furanone.

Abstract

169ChemInform Abstract The β-acetoxy-α-bromolactones (I) are converted to the olefins (IIa) and (IIb) which are hydrolyzed to form the (S)-5-hydroxymethyl-2(5H)-furanone (IIc). This compound is a starting material for the synthesis of various natural products.

Synthetic approaches to butenolides

“…Other Wittig-based methods leading to /I-substituted butenolides 48 include an intramolecular version in which the likely intermediate 47 in the Bestmann method is prepared in stepwise manner by ester formation between an a-bromo-acid and an a-bromoketone followed by quaternization and elimination of hydrogen bromide.32 Overall yields are generally high in both models and in cardenolide synthesis, but the methodology is not appropriate for the elaboration of ring-fused butenolides, starting with cyclic a-bromoketones. tXPPh3 47 49 48…”