Reinvestigation of a synthesis of (R,S)-mevalonolactone
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1417-1420
- https://doi.org/10.1039/p19830001417
Abstract
An n.m.r. study of the reaction of 3-hydroxy-3-methylpentane-1,5-dioic acid (5) with excess of [2H6]-acetic anhydride is described. It has shown that 3-hydroxy-3-methylpentane-1,5-dioic acid anhydride (2), previously described by Scott and Shishido 1 as an intermediate in their synthesis of [3′-13C]mevalonolactone, is formed only transiently, along with 3-acetoxy-3-methylpentane-1,5-dioic acid (6). Both intermediates eventually give 3-acetoxy-3-methylpentane-1,5-dioic acid anhydride (3). To obtain (R,S)-mevalonolactone, sodium borohydride reduction of 3-hydroxy-3-methylpentane-1,5-dioic acid anhydride (2), prepared from the diacid (5) and N,N-dicyclohexylcarbodi-imide, is shown to be better than reduction of 3-acetoxy-3-methylpentane-1,5-dioic acid anhydride (3).This publication has 1 reference indexed in Scilit:
- Studies in terpenoid biosynthesis. Part XVII. Biosynthesis of the sesquiterpenoids cyclonerodiol and cyclonerotriolJournal of the Chemical Society, Perkin Transactions 1, 1976