Synthesis of highly functionalized cyclopentanes as precursors of hydroxylated azidocarbonucleosides

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Abstract

Regio- and stereoisomers of functionalized azido amino alcohols with a cyclopentane skeleton were synthesized in enantiomerically pure forms. Enzymatic ring cleavage of racemic2-azabicyclo[2.2.1]hept-5-en-3-one gave the corresponding amino acid and one enantiomer of the lactam stereospecifically. These were protected by esterification and carbamoylation, and then epoxidized. The resulting oxiranes underwent cleavage by sodium azide with complementary stereoselectivities. The regioisomeric products were easily separated by crystallization or column chromatography.

Original languageEnglish
Article numberT13309SS
Pages (from-to)153-160
Number of pages8
JournalSynthesis
Issue number1
DOIs
Publication statusPublished - Feb 5 2010

Keywords

  • Amino acids
  • Amino alcohols
  • Carbocycles
  • Enzymes
  • Nucleosides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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