A short high yielding synthesis of the potent anti-VZV carbocyclic nucleoside analogue carba-BVDU

Article abstract of DOI:10.1080/15257779508010722

A short high yielding synthesis of the potent anti-varicella-zoster virus (VZV) carbocyclic nucleoside analogue carba-BVDU 1 starting from aminodiol 2 is described. Reaction of 2 with acyl carbamate 3 and subsequent ring closure under acidic conditions afforded 5-ethyl-2'-deoxy-4'a-carbauridine 5. In situ acetylation of 5 afforded 3',5'-di-O-acetyl-5-ethyl-2'-deoxy-4'a-carbauridine 6 in 78% overall yield from 2. Radical bromination of 6 with either bromine or NBS and subsequent treatment with triethylamine gave an efficient conversion to 3',5'-di-O-acetyl-5-(E)-(2-bromovinyl)-2'-deoxy-4'a- carbauridine 7. Deacetylation of 7 afforded 1 in an overall 45-53% yield from 2.

Full text of DOI:10.1080/15257779508010722

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Nucleosides and Nucleotides
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A Short High Yielding Synthesis of
the Potent Anti-VZV Carbocyclic
Nucleoside Analogue Carba-BVDU
P. G. Wyatt a , A. S. Anslow b , B. A. Coomber a , R. P.C.
Cousins a , D. N. Evans a , V. S. Gilbert a , D. C. Humber a ,
I. L. Paternoster b , S. L. Sollis a , D. J. Tapolczay b & G. G.
Weingarten a
a Department of Medicinal Chemistry II , Glaxo Wellcome plc,
Glaxo Wellcome Medicines Research Centre , Gunnels Wood
Road, Stevenage, Herts, SG1 2NY, UK
b Process Research Department , Glaxo Wellcome plc, Glaxo
Wellcome Medicines Research Centre , Gunnels Wood Road,
Stevenage, Herts, SG1 2NY, UK
Published online: 24 Sep 2006.
To cite this article: P. G. Wyatt , A. S. Anslow , B. A. Coomber , R. P.C. Cousins , D. N. Evans ,
V. S. Gilbert , D. C. Humber , I. L. Paternoster , S. L. Sollis , D. J. Tapolczay & G. G. Weingarten
(1995) A Short High Yielding Synthesis of the Potent Anti-VZV Carbocyclic Nucleoside Analogue
Carba-BVDU, Nucleosides and Nucleotides, 14:9-10, 2039-2049, DOI: 10.1080/15257779508010722
To link to this article: http://dx.doi.org/10.1080/15257779508010722
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