The shortest synthetic route to puromycin analogues using a modified Robins approach

J Org Chem. 2011 Apr 1;76(7):2253-6. doi: 10.1021/jo102178h. Epub 2011 Mar 1.

Abstract

We are reporting on the utility of commercial vinyl isocyanate for a practical synthetic route from adenosine to N(6)-bis-demethylpuromycin in seven steps and 65% overall yield. A clean one-pot conversion of 3'-bromo-2'-carbamoyl derivative 8 to 3'-amino-3'-deoxyadenosine derivative 10 is the main feature of this synthetic pathway. This synthesis is the shortest synthetic route toward 3'-(aminoacylamido)deoxyadenosines to date.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Deoxyadenosines / chemical synthesis*
  • Deoxyadenosines / chemistry
  • Indicators and Reagents / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Puromycin / analogs & derivatives*
  • Puromycin / chemical synthesis*
  • Puromycin / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Deoxyadenosines
  • Indicators and Reagents
  • N(6)-bis-demethylpuromycin
  • 3'-amino-3'-deoxyadenosine
  • Puromycin