Studies in terpenoid biosynthesis. Part 27. The acetate and mevalonate labelling patterns of the sesquiterpenoid, alliacolide

Abstract

The enrichment and labelling patterns of alliacolide biosynthesized by Marasmius alliaceus from [1-¹³C]acetate and [1,2-¹³C₂]acetate, have been used to define the isoprene units. The sites of labelling of alliacolide by [2-²H₃]acetate and by [2-²H₂]-, [4-²H₂]-, and [5-²H₂]-mevalonates have been determined. The occurrence of hydrogen rearrangements to C-1 and from C-5 to C-6 during the biosynthesis has been demonstrated by ²H n.m.r. experiments.