Total Synthesis of (−)-Cylindricine C

Abstract

(-)-Cylindricine C has been synthesized from commercially available (<i>S</i>)-(-)-1,2,4-butanetriol in 11 steps with an overall yield of 12%. The key step utilizes a CrCl₂ reduction of an azide to form the corresponding amine with a subsequent double Michael addition to create the tricyclic skeleton of cylindricine from a monocyclic substrate.