Multi-step reaction with 12 steps
1.1: 92 percent / LiAlH4 / tetrahydrofuran / 0 °C
2.1: Et3N; DMAP / CH2Cl2 / 2 h / 0 °C
3.1: NaH / tetrahydrofuran / 0.17 h
3.2: n-BuLi / tetrahydrofuran; hexane / 0.17 h
3.3: 31.3 g / tetrahydrofuran; hexane / 1 h / 20 °C
4.1: 26.4 g / Et3N; MsN3 / acetonitrile
5.1: Rh2(S)-(PTPA)4 / CH2Cl2 / 12 h
5.2: 40 percent / aq. HCl; (S)-RuBINAP; H2 / tetrahydrofuran; methanol / 517.15 Torr
6.1: 85 percent / K2CO3 / acetone / 5 h / Heating
7.1: NaCN / hexamethylphosphoric acid triamide / 5 h / 75 - 80 °C
7.2: 75 percent / KOH / methanol / 0.08 h / 20 °C
8.1: NaOMe / methanol / 0.17 h / 0 °C
8.2: methanol / 26 °C / Heating
9.1: 52 percent / CuCN; n-BuLi; DIBAL / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1 h / -20 °C
10.1: 84 percent / H2 / Pd/C / ethanol / 2 h / 20 °C
11.1: 17.8 mg / L-Selectride / tetrahydrofuran / 3 h / -78 °C
12.1: 85 percent / Et3SiH; tris(pentafluorophenyl)boron / CH2Cl2 / 1 h
With
triethylsilane; dmap; lithium aluminium tetrahydride; n-butyllithium; dirhodium(II) tetrakis; tris(pentafluorophenyl)borate; sodium cyanide; hydrogen; sodium methylate; L-Selectride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; Methanesulfonyl azide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; acetone; acetonitrile;
DOI:10.1021/jo001519g