No abstract

An asymmetric 10-step synthesis is developed affording the title compound (XII) in 18% overall yield. The use of commercial sodium cyclopentadienide (I) improves the yield of (III) 3-fold. The enantiomer of (XII) and the adenine analogue are prepared in the same manner, whereas the thymine and iodouracil analogues are prepared prior to the development of the optimized oxidation/methylenation sequence ((VII) → (X)). The novel compound (XII) is a potent inhibitor of hepatitis B virus with relatively low cytotoxicity. -(BISACCHI, G. S.; CHAO, S. T.; BACHARD, C.; DARIS, J. P.; INNAIMO, S.; JACOBS, G. A.; KOCY, O.; LAPOINTE, P.; MARTEL, A.; MERCHANT, Z.; SLUSARCHYK, W. A.; SUNDEEN, J. E.; YOUNG, M. G.; COLONNO, R.; ZAHLER, R.; Bioorg. Med. Chem. Lett. 7 (1997) 2, 127-132; Bristol-Myers Squibb Pharm. Res. Inst., Princeton, NJ 08543, USA; EN)