An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen (1592U89)

Nucleosides Nucleotides Nucleic Acids. 2000 Jan-Feb;19(1-2):297-327. doi: 10.1080/15257770008033011.

Abstract

Ziagen, (1S,cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]- 2-cyclopentene-1-methanol, was synthesized from (1S,4R)-azabicyclo[2.2.1]hept-5-en-3-one by efficient processes which bypass problematic steps in earlier routes. 2-Amino-4,6-dichloro-5-formamidopyrimidine is a key intermediate which makes possible an efficient construction of the purine from a chiral cyclopentenyl precursor.

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Crystallography, X-Ray
  • Dideoxynucleosides / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Reverse Transcriptase Inhibitors / chemical synthesis*

Substances

  • Anti-HIV Agents
  • Dideoxynucleosides
  • Reverse Transcriptase Inhibitors
  • abacavir