Concise synthesis of the Erythrina alkaloid 3-demethoxyerythratidinone via combined rhodium catalysis

Org Lett. 2010 Dec 17;12(24):5704-7. doi: 10.1021/ol102535u. Epub 2010 Nov 19.

Abstract

The total synthesis of the erythrina alkaloid 3-demethoxyerythratidinone has been achieved via a strategy based on combined rhodium catalysis. The catalytic tandem cyclization effected by the interplay of alkynyl and vinylidene rhodium species allows for efficient access to the A and B rings of the tetracyclic erythrinane skeleton in a single step. The synthesis also features rapid preparation of the requisite precursor for the double ring closure and thus has been completed in only 7 total steps in 41% overall yield.

Publication types

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

MeSH terms

  • Catalysis
  • Cyclization
  • Erythrina / chemistry*
  • Indole Alkaloids / chemical synthesis*
  • Molecular Structure
  • Rhodium / chemistry*

Substances

  • 3-demethoxyerythratidinone
  • Indole Alkaloids
  • Rhodium