Multi-step reaction with 12 steps
1: 80 percent / LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 15 min; -10 deg C, 2 h
2: 74 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
3: H2 / Rh(I)(NBD)(DIPHOS-4)(+)*BF4(-)
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 10 min, 2.) CH2Cl2, -78 deg C, 20 min; 0 deg C, 30 min
6: 83 percent / 2,6-lutidine / CH2Cl2 / 4.5 h / Ambient temperature
7: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 2.) reflux, 8 h
8: 97 percent / 1 M aq. NaClO2, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1.) 0 deg C, 15 min, 2.) r.t., 2.5 h
9: 89 percent / 48percent aq. HF / acetonitrile; tetrahydrofuran / 48 h / Ambient temperature
10: 86 percent / benzenesulfonyl chloride, pyridine / 22 h / 0 °C
11: 61 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 10 min, 2.) 0 deg C, 5.5 h
12: 1.) O3, 2.) 30percent aq. H2O2 / 1.) EtOAc, -78 deg C, 2.) glac. AcOH, r.t., 72 h
With
pyridine; 2,6-dimethylpyridine; sodium chlorite; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; dimethylsulfide; hydrogen fluoride; hydrogen; dihydrogen peroxide; ozone; dimethyl sulfoxide; triethylamine; benzenesulfonyl chloride; lithium diisopropyl amide;
{(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF4;
In
tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00091a022