Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B

J Org Chem. 2009 Sep 4;74(17):6784-91. doi: 10.1021/jo901100m.

Abstract

An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R = n-C(7)H(15), R' = n-Pr) and 14 by the present enantioselective synthesis.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Alkenes / chemistry
  • Animals
  • Chemistry, Organic / methods*
  • Chromatography, Gas / methods
  • Drug Design
  • Kinetics
  • Models, Chemical
  • Poisons / chemistry
  • Pyrroles / chemistry
  • Pyrrolizidine Alkaloids / chemistry*
  • Ranidae
  • Spectroscopy, Fourier Transform Infrared / methods
  • Stereoisomerism

Substances

  • Alkaloids
  • Alkenes
  • Poisons
  • Pyrroles
  • Pyrrolizidine Alkaloids
  • xenovenine