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Synthesis of desired N-nitrosylated methyl esters 7a–m. Reagents and conditions: (i) H2SO4 (cat.), MeOH, 80 °C, 24 h, 96%; (ii) morpholine (3 eq.), MeCN, r.t., 24 h, 99%; (iii) Pd/C (10% w/w), H2 (1 atm.), EtOAc, r.t., 24 h, 97%; (iv) (Step 1) 5a–m (2 eq.), MeOH, reflux, 24 h; (Step 2) NaBH4 (3 eq.), MeOH/THF (2:3), 35 °C, 24–72 h (53–95%, over two steps); (v) NaNO2 (1.05 eq.), p-TsOH (1.05 eq.), CH2Cl2, r.t., 24 h (63–94%).
