Enzymatic kinetic resolution of internal propargylic diols. Part I: a new approach for the synthesis of (S)-pent-2-yn-1,4-diol, a natural product from Clitocybe catinus.

Internal bis-substituted propargylic diols were subjected to enzymatic kinetic resolution promoted by CAL-B. Employing a two round sequence EKR, mono- and bis-acetoxy propargylic products were obtained in a high enantiomeric ratio (E > 200). The efficiently resolved chiral 8b was applied in a concise synthesis of (S)-1b, an optically active natural product produced by fungi Clitocybe catinus.