Multi-step reaction with 17 steps
1: imidazole / CH2Cl2 / 1 h / 0 °C
2: 1.) nBu2SnO, 2.) nBu4NBr / 1.) MeOH, 60 deg C, 1 h, 2.) C6H6, 80 deg C, 5 h
3: 95 percent / 2,6-lutidine / CH2Cl2 / 4 h / 0 °C
4: 1.) O3, 2.) PPh3 / 1.) CH2Cl2, -78 deg C, 2 h, 2.) CH2Cl2, 25 deg C, 18 h
5: benzene / 17 h / 25 °C
6: 100 percent / DIBAL / CH2Cl2 / 3 h / -78 °C
7: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH2Cl2; 2,2,4-trimethyl-pentane / 19 h / -25 °C
8: Et3N, SO3*pyr / CH2Cl2; dimethylsulfoxide / 2 h
9: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1 h
10: TBAF / tetrahydrofuran / 1 h / -20 - 0 °C
11: imidazole / dimethylformamide; CH2Cl2 / 3 h / 0 °C
12: 88 percent / 2,6-lutidine / CH2Cl2 / 1.) -78 deg C, 10 min, 2.) 25 deg C, 30 min
13: 1.) 9-BBN, 2.) H2O2, NaHCO3, H2O / 1.) THF, 0 deg C, 4 h, 2.) THF, 0 deg C, 4 h
14: SO3*pyr, Et3N / dimethylsulfoxide; CH2Cl2 / 2 h / 0 °C
15: benzene / 11 h / 25 °C
16: 88 percent / DIBAL / CH2Cl2 / 3 h / -78 °C
17: 97 percent / 4 Angstroem molecular sieves, (+)-DET, Ti(OiPr)4 / CH2Cl2; 2,2,4-trimethyl-pentane / 18 h / -25 °C
With
1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO3 complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; ozone; triethylamine; triphenylphosphine;
In
tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E