Total Synthesis of (-)-Cylindricine H.

Starting from ( R )-phenylglycinol-derived tricyclic lactam 1 , the enantioselective synthesis of (-)-cylindricine H is reported. From the stereochemical standpoint, the key steps are the stereoselective generation of the quaternary C 10 stereocenter, the stereoselective introduction of the C 4 acetoxy and C 2 butyl substituents taking advantage of the lactam carbonyl functionality, and the assembly of the pyrrolidine ring with the required functionalized one-carbon chain at C 13 by intramolecular opening of an epoxide.