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.

Automated summary

The enantioselective synthesis of (-)-cylindricine H from (R)-phenylglycinol-derived tricyclic lactam 1 is reported. Key steps include 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.