Intramolecular Redox-Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core.

ABSTRACT: Cyclic amines such as pyrrolidine undergo redox-annulations with 2-formylaryl malonates. Concurrent oxidative amine α-CH bond functionalization and reductive N-alkylation render this transformation redox-neutral. This redox-Mannich process provides regioisomers of classic Reinhoudt reaction products as an entry to the tetrahydroprotoberberine core, enabling the synthesis of (±)-thalictricavine and its epimer. An unusually mild amine-promoted dealkoxycarbonylation was discovered in the course of these studies.

SUBMITTER: Ma L 

PROVIDER: S-EPMC4808586 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature