Exercising regiocontrol in palladium-catalyzed asymmetric prenylations and geranylation: unifying strategy toward flustramines A and B

J Am Chem Soc. 2011 May 18;133(19):7328-31. doi: 10.1021/ja2020873. Epub 2011 Apr 26.

Abstract

Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio- and diastereoselectivity was obtained using π-geranylpalladium complexes.

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
  • Geranyltranstransferase / chemistry
  • Indole Alkaloids / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Prenylation
  • Stereoisomerism

Substances

  • Indole Alkaloids
  • Palladium
  • flustramine A
  • flustramine B
  • Geranyltranstransferase