Total Synthesis of (−)-Cylindricine H

[Image: see text] 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.