Multi-step reaction with 13 steps
1: 92 percent / zinc bromide / dimethylsulfoxide / 4 h
2: 26 percent / (S)-CBS catalyst; borane-dimethyl sulfide complex / 0 °C
3: 99 percent / 2,6-lutidine / CH2Cl2 / 0.75 h
4: 73 percent / p-toluenesulfonic acid; ethanol / 0 - 23 °C
5: 91 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 2 h
6: 53 percent / titanium tetrabromide; titanium tetraisopropoxide; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 2 h / -78 °C
7: 89 percent / 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 20 h
8: 73 percent / potassium hydroxide; water / acetonitrile; various solvent(s) / 14 h
9: 73 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0.75 h
10: 89 percent / 2-methyl-2-butene; sodium chlorite; monobasic sodium phosphate / 2-methyl-propan-2-ol; H2O / 2 h
11: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 23 °C
12: 75 percent / tributylphosphine; diisopropyl azodicarboxylate / toluene / 0.83 h
13: 78 percent / 18-crown-6 / toluene / 16 h / 110 °C
With
pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; potassium hydroxide; sodium chlorite; 2,6-di-tert-butyl-4-methylpyridine; 2-methyl-but-2-ene; 18-crown-6 ether; ethanol; tributylphosphine; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; water; titanium(IV) bromide; Dess-Martin periodane; toluene-4-sulfonic acid; zinc dibromide;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; tert-butyl alcohol;
5: Dess-Martin oxidation / 9: Dess-Martin oxidation / 10: Lindgren oxidation / 12: Mitsunobu reaction;
DOI:10.1021/jo070901r