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Synthesis from ethyl acetoacetate 41 of enantiomerically pure (N)-methanocarba-2′-deoxyguanosine 51 using an enzymatic resolution.25 Reagents and conditions: (a) (i) acrolein, LDA; (ii) TBDPSCl, imidazole; (b) TsN3, Et3N; (c) CuSO4, cyclohexane; (i) NaBH4, CH2Cl2–MeOH; (ii) LiAlH4, Et2O (e) vinyl acetate, Lipase PS-C; (f) (NH4)HF2, DMF–H2O; (g) 2-acetamide-6-chloropurine, Ph3P, DEAD; (h) 2N HCl, THF, 80 °C.
