An improved route to (3RS,5S)-[5-3H1]mevalonic acid

Abstract

The title compound has been synthesized, with specific radioactivity around 10 Ci mol^–1, by a synthesis using as stereospecific step the enzymic reduction of 3-methyl[1-³H]but-3-enal on liver alcohol dehydrogenase; this was followed by a chemical transformation of the product, (1S)-3-methyl[1-³H₁]but-3-en-1-ol, to mevalono-lactone via a bromohydrin and a cyanohydrin. 3-Methylbut-3-enal has been prepared and characterized for the first time, and the deuteriated alcohols, (1S)-3-methyl[1-²H₁]but-3-en-1-ol and (1S)-3-methyl[1-²H₁]but-2-en-1-ol, have been isolated: both are dextrorotatory.