Synthesis of novel purinyl-1'-homocarbanucleosides based on a cyclopenta[b]pyrazine system

Chem Pharm Bull (Tokyo). 2008 May;56(5):654-8. doi: 10.1248/cpb.56.654.

Abstract

cis-2,3-Diphenyl-6,7-dihydro-5H-cyclopenta[b]pyrazine-5,7-dimethanol, prepared by Diels-Alder reaction from cyclopentadiene and appropriately protected 2-imidazolone--followed by dihydroxylation, glycol protection, diamine deprotection, condensation with benzyl, glycol deprotection, oxidative cleavage and reduction--, was used to synthesize (+/-)-cis-([7-(6-chloro-9H-purin-9-yl)methyl]-2,3-diphenyl-6,7-dihydro-5H-cyclopenta[b]pyrazin-5-yl)methanol, a key intermediate for novel 1'-homocarbanucleosides based on a cyclopenta[b]pyrazine scaffold as shown by its conversion into several 6-substituted purinyl derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Hydroxylation
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Oxidation-Reduction
  • Purines
  • Pyrazines / chemical synthesis*
  • Spectrophotometry, Infrared
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Purines
  • Pyrazines
  • cis-((7-(6-chloro-9H-purin-9-yl)methyl)-2,3-diphenyl-6,7-dihydro-5H-cyclopenta(b)pyrazin-5-yl)methanol
  • cis-2,3-diphenyl-6,7-dihydro-5H-cyclopenta(b)pyrazine-5,7-dimethanol