Multi-step reaction with 20 steps
1.1: 91 percent / p-TsOH*H2O / 16 h / 20 °C
2.1: disiamylborane / tetrahydrofuran / 16 h / -20 °C
2.2: 76 percent / aq. NaOH; H2O2 / tetrahydrofuran / 3 h
3.1: 89 percent / imidazole / CH2Cl2 / 16 h / 20 °C
4.1: 95 percent / LiAlH4 / diethyl ether / 0.25 h / 20 °C
5.1: 88 percent / NMO / TPAP / acetone / 2 h
6.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C
6.2: 89 percent / tetrahydrofuran / 2 h / 20 °C
7.1: 96 percent / aq. HOAc / tetrahydrofuran / 16 h / 60 °C
8.1: 83 percent / SO3*pyridine; DMSO / CH2Cl2 / 3 h / 20 °C
9.1: 62 percent / CrCl2 / NiCl2 / dimethylformamide / 18 h / 50 °C
10.1: LiAlH4 / diethyl ether / 0.5 h / 20 °C
11.1: imidazole / dimethylformamide
12.1: 83 percent / pyridine / CH2Cl2
13.1: 71 percent / CSA / methanol / 0 °C
14.1: 98 percent / NMO / TPAP / acetone
15.1: tetrahydrofuran / 0 °C
16.1: 87 percent / Cy3P-RuCl2(=CHPh)-((Ms)N-CH2-CH2-N(MS)) / toluene / 16 h / 70 °C
17.1: 66 percent / aq. OsO4; DMAP / 2-methyl-propan-2-ol / 0.5 h / 20 °C
18.1: 62 percent / Dess-Martin reagent / CH2Cl2 / -20 - 20 °C
19.1: Cu(OAc)2 / methanol
20.1: Ag2O / dimethylformamide
With
pyridine; 1H-imidazole; chromium dichloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; copper diacetate; pyridine-SO3 complex; camphor-10-sulfonic acid; bis-(1,2-dimethylpropyl)borane; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; silver(l) oxide;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrapropylammonium perruthennate; nickel dichloride;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
6.2: Wittig olefination / 15.1: Wittig olefination;
DOI:10.1039/b202020n