Total Synthesis of (-)-Strempeliopine

J Am Chem Soc. 2021 Aug 11;143(31):12412-12417. doi: 10.1021/jacs.1c06913. Epub 2021 Jul 29.

Abstract

A total synthesis of (-)-strempeliopine is disclosed that enlists a powerful SmI2-mediated and BF3·OEt2-initiated dearomative transannular radical cyclization onto an indole by an N-acyl α-aminoalkyl radical that is derived by single electron reduction of an in situ generated iminium ion for formation of a quaternary center and the strategic C19-C2 bond in its core structure.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Cyclization
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Indole Alkaloids
  • strempeliopine