Multi-step reaction with 15 steps
1.1: (Sia)2BH / tetrahydrofuran / 0 °C
1.2: aq. H2O2; NaHCO3 / tetrahydrofuran
2.1: CSA / 1,2-dichloro-ethane / 20 °C
3.1: 100 percent / H2 / Pd(OH)2/C / ethyl acetate / 20 °C
4.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -80 - -60 °C
5.1: 4.8 g / toluene / -80 - -70 °C
6.1: 4.26 g / NaH / tetrahydrofuran; dimethylformamide / 7 h / 20 °C
7.1: aq. NMO; OsO4 / 2-methyl-propan-2-ol / 48 h / 20 °C
7.2: NaIO4 / 2-methyl-propan-2-ol; H2O / 1 h / 20 °C
8.1: 280 mg / NaH2PO4*2H2O; NaClO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 3 h / 20 °C
9.1: 90 percent / Et3N; 2,4,6-trichlorobenzoyl chloride; DMAP / toluene / 5.5 h / 40 °C
10.1: 80 percent / Cp2TiCl2; Mg; P(OEt)3 / tetrahydrofuran / 1 h / Heating
11.1: dimethyldioxirane (DMDO) / CH2Cl2; acetone / 0.5 h / -78 - -45 °C
12.1: 8.7 mg / LiBHEt3 / tetrahydrofuran / 3 h / 0 °C
13.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
14.1: 62 percent / TfOH / CH2Cl2; hexane / 30 h / 20 °C
15.1: 81 percent / Et3SiH; BF3*OEt2 / CH2Cl2 / 1 h / -62 - -20 °C
With
triethylsilane; dmap; bis(cyclopentadienyl)titanium dichloride; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; 2-methyl-but-2-ene; oxalyl dichloride; trifluorormethanesulfonic acid; (Sia)2BH; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium perchlorate; hydrogen; 3,3-dimethyldioxirane; sodium hydride; lithium triethylborohydride; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; triethyl phosphite;
palladium dihydroxide;
In
tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
4.1: Swern oxidation;
DOI:10.1021/jo049877x