Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: synthesis of (+/-)-2-epi-pumiliotoxin C.

ABSTRACT: Intramolecular Diels-Alder cycloaddition of N-substituted oxazolone triene I allows direct entry to the functionalized octahydroquinoline II. Further manipulation of this framework by stereo- and regioselective introduction of the 5-methyl substituent, followed by excision of the carbamate, yields (+/-)-2-epi-pumiliotoxin C.

SUBMITTER: Fearnley SP 

PROVIDER: S-EPMC2872181 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature