Multi-step reaction with 12 steps
1.1: diphenylphosphoryl azide; N,N-diisopropylethylamine / toluene / 4 h / 60 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C
2.2: 3.60 g / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C
3.1: 74 percent / NaIO4; KMnO4; NaHCO3 / acetone; H2O / 6 h / 20 °C
4.1: 100 percent / H2 / Pd/C / methanol / 5 h / 20 °C / 760 Torr
5.1: 1,2-dichloro-ethane / 0.42 h
6.1: 387 mg / sodium triacetoxyborohydride / 1,2-dichloro-ethane / 5 h / 20 °C
7.1: acetonitrile / 2 h / 20 °C
8.1: 230 mg / tetrabutylammonium fluoride / acetonitrile / 4 h / 60 °C
9.1: piperidine / dimethylformamide / 1 h / 20 °C
10.1: 80 percent / HBTU; N,N-diisopropylethylamine / dimethylformamide / 2 h / 20 °C
11.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C
12.1: 98 mg / Dess-Martin periodinane / CH2Cl2 / 12 h / 20 °C
With
piperidine; potassium permanganate; sodium periodate; n-butyllithium; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; Dess-Martin periodane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
1.1: Curtius rearrangement;
DOI:10.1021/jo0508954