Formal synthesis of (±)-morphine

Chem Asian J. 2013 Jun;8(6):1105-9. doi: 10.1002/asia.201300139. Epub 2013 Mar 18.

Abstract

The pain ends here: A novel synthetic strategy for the construction of (±)-morphine rings B and E was developed, in which SmI2 -promoted reductive coupling/desulfurization and tandem alcoholysis/oxa-Michael addition featured as the key steps for the assembly of the C9-C14 and C5-O bonds, respectively. Asymmetric tandem alcoholysis/oxa-Michael addition was also feasible for the enantiocontrolled synthesis of morphine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Analgesics, Opioid / chemical synthesis*
  • Analgesics, Opioid / chemistry
  • Chemistry Techniques, Synthetic / methods*
  • Cyclization
  • Cycloaddition Reaction
  • Mannich Bases
  • Molecular Structure
  • Morphine / chemical synthesis*
  • Morphine / chemistry
  • Stereoisomerism

Substances

  • Analgesics, Opioid
  • Mannich Bases
  • Morphine