Multi-step reaction with 12 steps
1.1: 94 percent / TMSOTf / acetonitrile / 0.5 h / -23 °C
2.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 22 °C
3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C
3.2: 91 percent / tetrahydrofuran / 0.33 h / 22 °C
4.1: 100 percent / diisobutylaluminum hydride / cyclohexane; CH2Cl2 / 0.33 h / -78 °C
5.1: 94 percent / titanium tetraisopropoxide; tert-butyl hydroperoxide; molecular sieves 4 Angstroem / D-(-)-diisopropyl tartrate / CH2Cl2; decane / -20 - 0 °C
6.1: pyridine; Dess-Martin periodinane / benzene; acetonitrile / 0.67 h / 22 °C
7.1: tert-butyllithium / pentane; diethyl ether / 1 h / -78 °C
7.2: 75 percent / pentane; diethyl ether / 0.75 h / -78 °C
8.1: formic acid / tetrahydrofuran; H2O / 0.75 h / 22 °C
9.1: 89 percent / DDQ / CH2Cl2 / 1 h / 22 °C / pH 7
10.1: pyridine; Dess-Martin periodinane / benzene; acetonitrile / 0.67 h / 22 °C
11.1: 100 percent / 2-methyl-2-butene; sodium chlorite; sodium dihydrogen phosphate / 2-methyl-propan-2-ol; H2O / 1 h / 22 °C
12.1: 88 percent / DMAP; 2,4,6-trichlorobenzoyl chloride / CHCl3 / 1 h / -40 - 22 °C
With
pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; formic acid; sodium dihydrogen phosphate; 2-methyl-but-2-ene; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
D-(-)-diisopropyl tartrate;
In
tetrahydrofuran; diethyl ether; decane; dichloromethane; chloroform; cyclohexane; water; acetonitrile; tert-butyl alcohol; pentane; benzene;
2.1: Swern oxidation / 3.2: Horner-Emmons reaction / 5.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol051415y