Multi-step reaction with 9 steps
1.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
2.1: (R,R)-1,2-diamino-1,2-diphenylethane-bis(toluenesulfonamide); boron tribromide / CH2Cl2 / 6 h / 20 °C
2.2: 85 percent / CH2Cl2 / 2 h / -78 °C
3.1: 99 percent / pyridine / 48 h / 20 °C
4.1: 99 percent / KOH / bis-(2-methoxy-ethyl) ether; ethane-1,2-diol / 1.5 h / 40 °C
5.1: borane-dimethyl sulfide / tetrahydrofuran / 0 - 20 °C
5.2: 83 percent / aq. NaOH; aq. H2O2; ethanol / tetrahydrofuran / 2 h / 20 °C
6.1: 95 percent / PPh3; imidazole; I2 / tetrahydrofuran / 0 - 20 °C
7.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -30 °C
7.2: 4.89 g / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h
8.1: 3.26 g / sodium amalgam / ethanol / 0 - 20 °C
9.1: 95 percent / aq. HOAc / 3 h / 50 - 55 °C
With
1H-imidazole; potassium hydroxide; sodium amalgam; n-butyllithium; dimethylsulfide borane complex; (R,R)-1,2-diamino-1,2-diphenylethane-bis(toluenesulfonamide); iodine; boron tribromide; Dess-Martin periodane; acetic acid; triphenylphosphine;
In
tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; diethylene glycol dimethyl ether; ethylene glycol;
DOI:10.1021/jo0605086