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

Tony K.M. Shing; Anthony W.H. Wong; Huiyan Li; Z. F. Liu; Paul K.S. Chan

doi:10.1039/c4ob01763c

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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

4 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 language	English
Pages (from-to)	9439-9445
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	46
DOIs	https://doi.org/10.1039/c4ob01763c
Publication status	Published - 2014 Dec 14

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Wong, Anthony W.H.

AU - Li, Huiyan

AU - Liu, Z. F.

AU - Chan, Paul K.S.

PY - 2014/12/14

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AB - 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.

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

Abstract

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