Synthesis of (+/-)-3H-epivincamine via a Rh(II)-triggered cyclization/cycloaddition cascade

Org Lett. 2007 Aug 16;9(17):3249-52. doi: 10.1021/ol071173x. Epub 2007 Jul 21.

Abstract

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Antihypertensive Agents / chemical synthesis
  • Cyclization
  • Rhodium / chemistry*
  • Vasodilator Agents / chemical synthesis
  • Vincamine / chemical synthesis*

Substances

  • Antihypertensive Agents
  • Vasodilator Agents
  • Vincamine
  • Rhodium