Multi-step reaction with 23 steps
1: p-TsOH / benzene / Heating
2: 74 percent / (i-Bu)2AlH / toluene / 1 h / -78 °C
3: 90 percent / PhCMe2O2H, (-)-DIPT, Ti(O-i-Pr)4, 4A molecular sieves / CH2Cl2 / 22 h / -20 °C
4: 71 percent / diethyl ether / 0 - 25 °C
5: 90 percent / py-DMAP / CH2Cl2 / 2 h / 25 °C
6: 86 percent / pyridinium p-toluenesulfonate (PPTS) / H2O; tetrahydrofuran / 36 h / 50 °C
7: 93 percent / (i-Pr)2NEt / CH2Cl2 / 4 h / Heating
8: 85 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C
9: 1.) Ac2O, Et3N, DMAP, 2.) DBU / 1.) CH2Cl2, 25 deg, 2 h, 2.) 25 deg C, 1 h
10: 93 percent / tetrahydrofuran / 1 h / 0 °C
11: 87 percent / Et3N / CH2Cl2 / -78 - 25 °C
12: 90 percent / 2KHSO5*KHSO4*K2SO4 (Oxone) / methanol; H2O / 48 h / 25 °C
13: 92 percent / (NH4)2Ce(NO3)6 / acetonitrile; H2O / 1 h / 25 °C
14: 82 percent / 2,6-lutidine / CH2Cl2 / 0 °C
15: 77 percent / LiAlH4 / tetrahydrofuran / 0 °C
16: 35 percent / 2.5percent Na(Hg), Na2HPO4 / methanol / 2 h / 25 °C
17: 90 percent / (COCl)2, Et3N / dimethylsulfoxide; CH2Cl2 / -78 - 25 °C
18: 98 percent / toluene / 2 h / Heating
19: 94 percent / (i-Bu)2AlH / toluene / 0.5 h / -75 °C
20: 93 percent / N-chlorosuccinimide, Me2S / CH2Cl2 / 0.5 h / 0 - 25 °C
21: 84 percent / dimethylformamide / 48 h / 25 °C
22: 1.) n-BuLi / 1.) THF, -78 deg C, 0.5 h
23: 85 percent / NaOMe, Na2HPO4 / methanol / 0.5 h / 0 °C
With
2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; potassium sulfate; potassium hydrogensulfate; disodium hydrogenphosphate; N-chloro-succinimide; lithium aluminium tetrahydride; potassium peroxomonosulfate; n-butyllithium; sodium amalgam; oxalyl dichloride; ammonium cerium(IV) nitrate; dimethylsulfide; Cumene hydroperoxide; 4-(dimethylamino)pyridine in pyridine; 4 A molecular sieve; sodium methylate; pyridinium p-toluenesulfonate; acetic anhydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1021/ja00160a051