Asymmetric synthesis of (-)-1-hydroxyquinolizidinone, a common intermediate for the syntheses of (-)-homopumiliotoxin 223G and (-)-epiquinamide

Org Lett. 2007 Nov 8;9(23):4705-8. doi: 10.1021/ol701952y. Epub 2007 Oct 12.

Abstract

The short and efficient asymmetric synthesis of (-)-1-hydroxyquinolizidinone was achieved in seven steps and 25.2% overall yield from readily available 5-chloropentanal. It is a key intermediate in the formal syntheses of (-)-homopumilotoxin 223G and (-)-epiquinamide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Imines / chemistry
  • Indolizines / chemical synthesis*
  • Indolizines / chemistry
  • Molecular Structure
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Quinolizidines / chemical synthesis*
  • Quinolizidines / chemistry
  • Quinolizines / chemical synthesis*
  • Quinolizines / chemistry
  • Stereoisomerism
  • Sulfonium Compounds / chemistry

Substances

  • 1-hydroxyquinolizidinone
  • Alkaloids
  • Imines
  • Indolizines
  • Piperidines
  • Quinolizidines
  • Quinolizines
  • Sulfonium Compounds
  • epiquinamide
  • homopumiliotoxin 223G
  • sulfinimine