Scheme 3.
Reagents and conditions: a Me2SO4, NaOH, H2O, 0 °C to r.t.; b H2, Pd, THF, 45 °C; c LiAlH4, Et2O, 0 °C; d H3PO4, EtOH, 60–70 °C; e 49, Et3N, benzene, tert-amylalcohol, reflux; f MeI, K2CO3, acetone, r.t.; g 51, 175ºC; h H2SO4, MeOH, reflux; CH2N2; i tBuOK, tBuOH, benzene, r.t.; j NaOH, H2O, MeOH, reflux; k OsO4, py, Et2O, r.t, KClO3, NaHCO3, MeOH, 100 °C; l NaOH, H2O, reflux; m powdered quartz glass, 260–270 °C; n TsCl, py, r.t.; o NH3, EtOH, 90–95 °C; p KOHaq., EtOH, 130 °C; q CH2N2, Et2O, MeOH, 0 °C; r NBS, benzoyl peroxide, CCl4, λν, reflux; s NH3, EtOH, H2O, 95–100 °C; t KOHaq., EtOH, 130 °C; u CH2N2, Et2O, CH2Cl2, MeOH, 0 °C; and v Ac2O, py, 100 °C