Multi-step reaction with 15 steps
1: 50percent NaOH / Bu4NHSO4 / benzene / 10 °C
2: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 2.) -78 deg C to 25 deg C
3: diethyl ether / -78 °C
4: CF3CO2H / benzene / Heating
6: 1.) BH3*THF, 2.) H2O2, aq OH(1-) / 1.) THF, -78 deg C to 0 deg C, 2.) 0 deg C to 25 deg C
7: i-Pr2NEt / CH2Cl2 / 0 °C
8: BF3*Et2O, EtSH / CH2Cl2 / 0 °C
9: PCC, 3 Angstroem molecular sieves / CH2Cl2
10: 87 percent / tetrahydrofuran / -78 - 25 °C
11: OsO4, NMMO / tetrahydrofuran / 24 h / 25 °C
12: PPTS / CH2Cl2 / 4.5 h / 25 °C
13: 1.) LiOH / 1.) aq. THF, 25 deg C, 12 h, 2.) THF-HOAc, 25 deg C, 1.5 h
14: LiAlH4 / diethyl ether / 20 h / 0 - 25 °C
15: i-Pr2NEt / CH2Cl2 / -24 °C
With
lithium hydroxide; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; borane-THF; dimethylsulfide; 3 A molecular sieve; boron trifluoride diethyl etherate; hydroxide; dihydrogen peroxide; pyridinium p-toluenesulfonate; ozone; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; trifluoroacetic acid; ethanethiol;
tetra(n-butyl)ammonium hydrogensulfate;
In
tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4039(00)95561-8