Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (-)-cermizine C and (-)-senepodine G.

ABSTRACT: A stereodivergent and diastereoselective transition-metal-catalyzed intramolecular hydroamidation of allenes and alkynes furnishing δ-vinyl-lactams is reported. Employing a rhodium catalyst allowed for the selective synthesis of the syn-δ-lactam. Conversely, a palladium catalyst led to the formation of the anti-δ-lactam in high selectivity. The new method shows high functional group compatibility and assorted synthetic transformations were demonstrated as well as its utility for the enantioselective formal total syntheses of (-)-cermizine C and (-)-senepodine G.

SUBMITTER: Schmidt JP 

PROVIDER: S-EPMC6430088 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature