Multi-step reaction with 14 steps
1: 78 percent / dicyclohexylcarbodiimide (DCC) / CH2Cl2 / 0.17 h
2: 81 percent / CH2Cl2 / 3 h / 25 °C
3: 45 percent / KF*2H2O / methanol; acetic acid / 17 h
4: 1.) 2-methyl-2-butene, BH3*THF; 2.) 30percent aq. H2O2, 2M NaOH / 1.) a.) 0 deg C, 1 h; b.) -23 deg C, 2.5 h; 2.) 0.5 h
5: 78 percent / Et3N, 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 5 h
6: 30percent HBr/AcOH, cyclohexene / 17 h
7: 90 percent / 4-methylmorpholine-N-oxide (MMNO) / OsO4 / acetone; H2O; 2-methyl-propan-2-ol / 4 h
8: 4-dimethylaminopyridine (DMAP), Et3N / CH2Cl2 / 0.17 h
9: DMSO/(COCl)2/Et3N, 4 Angstroem molecular sieves / CH2Cl2 / 1.67 h / -78 °C
10: NaBH4 / methanol / 0.25 h / 0 °C
11: 100 percent / 4-dimethylaminopyridine (DMAP), 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h
12: 100 percent / n-Bu3SnH, AIBN / benzene / 0.25 h / Heating
13: 94 percent / NaOMe / methanol / 5 h / Ambient temperature
14: 91 percent / Et3N, 4-dimethylaminopyridine (DMAP), MeSO2Cl / CH2Cl2 / 0.25 h
With
dmap; potassium fluoride; sodium hydroxide; sodium tetrahydroborate; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; hydrogen bromide; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium methylate; acetic acid; dimethyl sulfoxide; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide; cyclohexene;
osmium(VIII) oxide;
In
methanol; dichloromethane; water; acetic acid; acetone; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4020(01)88027-3