Carbocyclic nucleosides from enantiomeric, α-pinane-based aminodiols

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Abstract

Starting from (1R,2S,3S,5R)- and (1S,2R,3R,5S)-6,6-dimethylspiro[bicyclo[3. 1.1]heptane-2,2′-oxiran]-3-ol (-)-8 and (+)-8, two comparative syntheses were developed for pinane-based chiral carbocyclic nucleosides. The regioselective ring opening of the spiro-oxirane ring of (-)-8 and (+)-8 with NaN3 resulted in azidodiols (-)-9 and (+)-9. Catalytic reduction of (-)-9 and (+)-9 furnished chiral aminodiols (-)-10 and (+)-10, which were transformed by linear synthesis to purine-type nucleosides 16-18 through pyrimidine intermediates. Regioselective ring opening of the oxirane ring of (-)-8 and (+)-8 resulted in adenine-, cytosine- and uracil-based carbocyclic nucleosides 19-21 in a single-step synthesis.

Original languageEnglish
Pages (from-to)831-836
Number of pages6
JournalTetrahedron Asymmetry
Volume21
Issue number7
DOIs
Publication statusPublished - Apr 21 2010

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nucleosides
Nucleosides
Ethylene Oxide
rings
Purine Nucleosides
Heptanes
Sodium Azide
synthesis
Uracil
Cytosine
Heptane
Adenine
purines
uracil
adenines
pyrimidines
heptanes
pinane

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Carbocyclic nucleosides from enantiomeric, α-pinane-based aminodiols. / Szakonyi, Z.; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 21, No. 7, 21.04.2010, p. 831-836.

Research output: Contribution to journalArticle

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