Multi-step reaction with 15 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
With
pyridine; 1H-imidazole; chromium dichloride; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; pyridine-SO3 complex; camphor-10-sulfonic acid; bis-(1,2-dimethylpropyl)borane; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide;
tetrapropylammonium perruthennate; nickel dichloride;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;
6.2: Wittig olefination / 15.1: Wittig olefination;
DOI:10.1039/b202020n