Total synthesis of (+)-dibromophakellin

Angew Chem Int Ed Engl. 2009;48(21):3799-801. doi: 10.1002/anie.200806233.

Abstract

Two members of a family of pyrrole-imidazole marine alkaloids, (+)-dibromophakellin and the nonnatural congener (+)-phakellin, were synthesized enantioselectively from 4-hydroxy-L-proline. The chiral aminal at C10 was constructed efficiently by means of an Overman-type [3,3] sigmatropic rearrangement of an enamide (see scheme).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis
  • Alcohols / chemistry
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Molecular Structure
  • Piperazines / chemistry
  • Stereoisomerism

Substances

  • Alcohols
  • Heterocyclic Compounds, 4 or More Rings
  • Piperazines
  • dibromophakellin
  • phakellstatin