First synthesis of enantiomerically pure carbocyclic oxanosine as a potential chemotherapeutic agent

Synthesis of sugar-modified derivatives of the unusual nucleoside oxanosine and its carbocyclic analogs as potential inhibitors of HIV

“…Fairly recently we reported the first synthesis of 2 from D-ribonic acid γ-lactone. 8 However, this route involved some troublesome steps, so a more convenient and versatile route was required. In the present paper we describe an alternative new route to 2 starting from com-mercially available (Ϫ)-2-azabicyclo[2.2.1]hept-5-en-3-one 10.…”

“…OD) 3.70-3.72 (2H, m, 5Ј-H 2 ), 4.63 (1H, m, 4Ј-H), 6.06 (1H, ddd, J 1.5, 2.2 and 5.9 Hz, 3Ј-H), 6.43 (1H, ddd, J 1.5, 1.8 and 5.9 Hz, 2Ј-H), 6.79 (1H, ddd, J 1.5, 1.5 and 1 8. Hz, 1Ј-H) and 7.90 (s, 1H, 2-H); δ C (CD 3 OD; 75.5 MHz) 64.1 (C-5Ј), 89.7 (C-4Ј), 89.8 (C-1Ј), 112.2 (C-7a), 126.6 (C-3Ј), 135.6 (C-2Ј), 138.7 (C-2), 154.3 (C-3a), 156.0 (C-5) and 161.9 (C-7); m/z (EI) 250.0707.…”