Enantiospecific, stereospecific total synthesis of the oxindole alkaloid alstonisine

Org Lett. 2002 Nov 28;4(24):4237-40. doi: 10.1021/ol020170b.

Abstract

[reaction: see text] The total synthesis of alstonisine was accomplished in enantiospecific fashion in an overall yield of 12% (from tryptophan methyl ester) in 17 reaction vessels. The structure of alstonisine (1) has been determined by NOE spectroscopic experiments and was confirmed by single-crystal X-ray analysis.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry*
  • Alstonia / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Oxindoles
  • Spiro Compounds
  • Stereoisomerism

Substances

  • Alkaloids
  • Indoles
  • Oxindoles
  • Spiro Compounds
  • alstonisine