A stereocontrolled, enantiomerically specific total synthesis of thienamycin

Philos Trans R Soc Lond B Biol Sci. 1980 May 16;289(1036):191-5. doi: 10.1098/rstb.1980.0037.

Abstract

A versatile stereocontrolled total synthesis of thienamycin starting from L-aspartic acid is reported. Stereocontrol is achieved by potassium tri-sec-butylborohydride reduction of a thermodynamically formed 3 alpha-acetylazetidinone intermediate. The key [3.2.0] bicyclic ring system is prepared by a metal catalyzed carbene insertion reaction.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Lactams / chemical synthesis
  • Stereoisomerism
  • Thienamycins*

Substances

  • Anti-Bacterial Agents
  • Lactams
  • Thienamycins
  • thienamycin