Synthesis of (+/-)-3H-epivincamine via a Rh(II)-triggered cyclization/cycloaddition cascade.
A synthesis of (+/-)-3H-epivincamine is reported. Important steps include (1) a Rh(II)-catalyzed intramolecular [3+2]-cycloaddition of an alpha-diazo indolo amide, (2) a reductive ring opening of the cycloadduct, (3) a decarboethoxylation reaction, and (4) a base-induced keto-amide ring contraction.
England
Dylan B
DB
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Padwa
Albert
A
D000959:Antihypertensive Agents / Q000138:chemical synthesis; D003500:Cyclization; D012238:Rhodium / Q000737:chemistry*; D014665:Vasodilator Agents / Q000138:chemical synthesis; D014749:Vincamine / Q000138:chemical synthesis*
D000959:Antihypertensive Agents; D014665:Vasodilator Agents; D014749:Vincamine; D012238:Rhodium