Journal of the Chemical Society. Perkin transactions I p. 1417 - 1420 (1983)
Update date:2022-09-26
Topics:
Lewer, Paul
MacMillan, Jake
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 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).
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