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(a) OsO4 (0.1–0.3 mol%), N-methylmorpholine-N-oxide (3 eq.), tBuOH/H2O (1:1), 4 days; (b) NaIO4 (1.2 eq.), MeOH/H2O (3:1), 0.5–2 h; (c) Ph3PCHCO2Et (1.1 eq.), CH2Cl2, 16 h; (d) 18: DIBAL-H (3 eq.), CH2Cl2, −78 °C, 10 min, 19: DIBAL-H (2.2 eq.), toluene, −10 °C, 10 min; (e) Et3N (3 eq.), MsCl (1.2 eq.), morpholine (1.5 eq.), CH2Cl2, 0 °C, 2–18 h.
