First total synthesis of a naturally occurring iodinated 5'-deoxyxylofuranosyl marine nucleoside

Mar Drugs. 2012 Apr;10(4):881-9. doi: 10.3390/md10040881. Epub 2012 Apr 10.

Abstract

4-Amino-7-(5'-deoxy-β-D-xylofuranosyl)-5-iodo-pyrrolo[2,3-d]pyrimidine 1, an unusual naturally occurring marine nucleoside isolated from an ascidan, Diplosoma sp., was synthesized from D-xylose in seven steps with 28% overall yield on 10 g scale. The key step was Vorbrüggen glycosylation of 5-iodo-pyrrolo[2,3-d]pyrimidine with 5-deoxy-1,2-O-diacetyl-3-O-benzoyl-D-xylofuranose. Its absolute configuration was confirmed.

Keywords: Vorbrüggen glycosylation; marine nucleoside; pyrrolo[2,3-d]pyrimidine; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aquatic Organisms / chemistry*
  • Biological Products / chemistry*
  • Glycosylation
  • Hydrocarbons, Iodinated / chemical synthesis*
  • Hydrocarbons, Iodinated / chemistry*
  • Iodine / chemistry
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry*
  • Urochordata / chemistry*
  • Xylose / chemistry

Substances

  • Biological Products
  • Hydrocarbons, Iodinated
  • Nucleosides
  • Iodine
  • Xylose