Royal Society of Chemistry, Heterocyclic Chemistry Group, Lakeland Heterocyclic Symposium (10th), Held in Grasmere 9-13 May 1991
SUNDERLAND POLYTECHNIC (UNITED KINGDOM) SUNDERLAND United Kingdom
Pagination or Media Count:
Analogues of the natural nucleosides continue to provide most of todays clinically useful anti-viral drugs. Their anti-viral properties generally result from inhibition of one or more of the key viral processing enzymes, or from incorporation into viral DNA or RNA, and subsequent chain termination of nucleic acid synthesis. The early analogues generally involved changes in the natural bases, and only following the success of acyclovir 1, and then zidovudine 2, was attention turned in earnest to analogues in which the sugar ring was modified. During the eighties, cyclopentanoid nucleosides, such as carbovir, attracted immense attention, but one variant of the nucleoside analogue type remained relatively unexplored - that of substitution of the sugar ring oxygen by sulphur, to give thiolanes. Although the corresponding 4-thiafuranose sugars have been reported in the literature, examples of their transformation into nucleoside analogues have been relatively rare. In part this has been due to the lack of robust, general routes to 4-thianucleosides, and the subject of the presentation will be the development of just such a route.