Total Synthesis of (−)-Cylindricine C

(−)-Cylindricine C has been synthesized from commercially available ( S )-(−)-1,2,4-butanetriol in 11 steps with an overall yield of 12%. The key step utilizes a CrCl 2 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.