Biosynthesis of the Verrucarins and Roridins. Part 1. The transformation of mevalonic acid into verrucarinic acid. Evidence for a hydrogen 1,2‐shift. Verrucarins and roridins, 27th communication

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Abstract
Incorporation experiments using sodium [2‐14C]‐, [2‐3H]‐, (3R)‐[5‐14C]‐ and [2‐3H, 2‐14C]‐mevalonates and with mevalonates stereospecifically tritiated at C(2) demonstrate the transformation of mevalonic acid (8) into verrucarinic acid (5). Degradation experiments showed that this transformation occurs with a hydrogen 1, 2‐shift of the ‘pro‐2R’ hydrogen atom of mevalonate to C(3) of verrucarinate. A possible mechanistic pathway is discussed.