Total synthesis of the tetracyclic lupin alkaloid (+)-allomatrine

Org Lett. 2013 Sep 6;15(17):4596-9. doi: 10.1021/ol402198n. Epub 2013 Aug 27.

Abstract

(+)-Allomatrine (1) has been synthesized using an imino-aldol reaction and N-acyliminium cyclization as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enabled the staged formation of three C-C bonds, a C-N bond, and the four stereogenic centers within the target.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Matrines
  • Molecular Conformation
  • Molecular Structure
  • Quinolizines / chemical synthesis*
  • Quinolizines / chemistry
  • Sophora / chemistry
  • Stereoisomerism
  • Trimethylsilyl Compounds / chemistry

Substances

  • Alkaloids
  • Quinolizines
  • Trimethylsilyl Compounds
  • allomatrine
  • Matrines