Multi-step reaction with 14 steps
1.1: AD-mix-α / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
2.1: CSA / benzene; methanol / 32 h
2.2: H2 / Pd(OH)2 / ethanol / 12 h / 20 °C / 760 Torr
3.1: 98 percent / TFA / methanol / 0.83 h / Heating
4.1: 75 percent / NMO; 4 Angstroem molecular sieves; TPAP / 2-methyl-propan-2-ol; acetonitrile / 20 °C
5.1: pyridine / tetrahydrofuran; toluene / 0.75 h / -78 - 20 °C
5.2: 9-BBN / tetrahydrofuran; toluene / 0.5 h / 20 °C
5.3: 40 percent / NaBO3*4H2O / tetrahydrofuran; toluene / 2 h
6.1: Dess-Martin periodinane reagent / CH2Cl2 / 2.5 h / 20 °C
7.1: 77 percent / TiCl4 / CH2Cl2 / 0.33 h / -78 °C
8.1: 91 percent / pyridine; DMAP / 27 h / 20 °C
9.1: 99 percent / IBr / toluene; CH2Cl2 / 3 h / -80 °C
10.1: 90 percent / aq. LiOH / 1,2-dimethoxy-ethane / 13 h / 60 °C
11.1: 90 percent / pyridine; DMAP / CH2Cl2 / 16 h / 20 °C
12.1: 99 percent / pyridine; DMAP / 15 h
13.1: aq. LiOH / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C
14.1: 34.2 mg / benzene; methanol; hexane / 0.25 h / 20 °C
With
pyridine; dmap; lithium hydroxide; AD-mix-α; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; iodine(I) bromide; titanium tetrachloride; Dess-Martin periodane; trifluoroacetic acid;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4020(02)00050-9