Conformationally locked bicyclo[4.3.0]nonane carbanucleosides: Synthesis and bio-evaluation

Tony Kung Ming Shing, Anthony W.H. Wong, Huiyan Li, Z. F. Liu, Paul K.S. Chan

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

d-Ribose was converted into 3 novel carbobicyclic nucleosides bearing a bicyclo[4.3.0]nonane framework in 16-19 steps with 5-12% overall yields involving a Wittig olefination and an intramolecular Diels-Alder reaction as the key steps. The present synthesis also provides an efficient entry for chiral hydrindenones. The conformation studies of these carbanucleosides and their bio-evaluation as potential antiviral agents are reported.

Original languageEnglish
Pages (from-to)9439-9445
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number46
DOIs
Publication statusPublished - 2014 Dec 14
Externally publishedYes

Fingerprint

Bearings (structural)
nonanes
Ribose
Cycloaddition Reaction
Nucleosides
Antiviral Agents
Conformations
ribose
Diels-Alder reactions
nucleosides
evaluation
synthesis
entry
nonane

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Conformationally locked bicyclo[4.3.0]nonane carbanucleosides : Synthesis and bio-evaluation. / Shing, Tony Kung Ming; Wong, Anthony W.H.; Li, Huiyan; Liu, Z. F.; Chan, Paul K.S.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 46, 14.12.2014, p. 9439-9445.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Wong, Anthony W.H. ; Li, Huiyan ; Liu, Z. F. ; Chan, Paul K.S. / Conformationally locked bicyclo[4.3.0]nonane carbanucleosides : Synthesis and bio-evaluation. In: Organic and Biomolecular Chemistry. 2014 ; Vol. 12, No. 46. pp. 9439-9445.
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