STUDIES DIRECTED TOWARD ANTI-HIV COMPOUNDS

Reaction of beta-D-xylofuranosylthymine with diphenylcarbonate/NaHCO3/ DMF provided 2,2'-anhydro-beta-D-arabinofuranosylthymine with concomi tant isomerisation at C-3'. This novel rearrangement has been employed in the synthesis of beta-thymidine, a precursor for anti-AIDS drugs - AZT and d(4)T. The synthetic studies toward the anti-HIV marine guani dine alkaloid batzelladine A has also been described. The left hand bi cyclic guanidine segment is obtained from ethylacetoacetate by involvi ng tethered Biginelli condensation. Simultaneously the right hand tric yclic guanidine segment was synthesised stereospecifically from -(tert -butyldimethylsilyloxy)ethyl]-2-azetidinone.