Multi-step reaction with 17 steps
1.1: PPh3 / acetonitrile; toluene / 0.17 h / 0 °C
1.2: imidazole / acetonitrile; toluene / 0.25 h / 0 °C
1.3: 75 percent / I2 / acetonitrile; toluene / 0.5 h / 0 °C
2.1: 84 percent / toluene / 16 h / 100 °C
3.1: t-BuOK / tetrahydrofuran; toluene / 0.5 h / 70 °C
3.2: 95 percent / tetrahydrofuran; toluene / 6 h / 70 °C
4.1: 98 percent / H2 / PtO2 / ethyl acetate / 0.67 h / 760 Torr
5.1: 76 percent / p-TsOH / acetone / 7 h / 40 °C
6.1: LDA / tetrahydrofuran / 1 h / -78 - 0 °C
6.2: 84 percent / HMPA / 0.17 h / -78 °C
7.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
7.2: 95 percent / tetrahydrofuran / 1.5 h / 0 - 20 °C
8.1: 71 percent / CrCl2 / NiCl2 / dimethylformamide / 18 h / 50 °C
9.1: LiAlH4 / diethyl ether / 0.5 h / 20 °C
10.1: imidazole / dimethylformamide
11.1: 94 percent / pyridine / CH2Cl2
12.1: 92 percent / CSA / methanol / 0 °C
13.1: 91 percent / NMO / TPAP / acetone
14.1: tetrahydrofuran / 0 °C
15.1: 99 percent / Cy3P-RuCl2(=CHPh)-((Ms)N-CH2-CH2-N(MS)) / toluene / 16 h / 70 °C
16.1: 74 percent / aq, OsO4; DMAP / 2-methyl-propan-2-ol / 0.5 h / 20 °C
17.1: 72 percent / Dess-Martin reagent / CH2Cl2 / -20 - 20 °C
With
pyridine; 1H-imidazole; chromium dichloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triphenylphosphine; lithium diisopropyl amide;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; platinum(IV) oxide; tetrapropylammonium perruthennate; nickel dichloride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;
14.1: Wittig olefination;
DOI:10.1039/b202020n