Multi-step reaction with 20 steps
1: 89 percent / AlMe3 / tetrahydrofuran
2: 100 percent / 2,6-lutidine / CH2Cl2
3: 92 percent / H2 / Pd(OH)2/C / ethanol
4: 98 percent / SO3*pyridine, Et3N / dimethylsulfoxide
5: 79 percent / ZnCl2 / diethyl ether
6: 91 percent / DIBAL / tetrahydrofuran
7: 99 percent / TsOH*H2O / methanol
8: 1.) t-BuLi, HMPA / 1.) THF, 2.) THF
9: 80 percent / PhI(CF3CO3)2 / methanol; H2O
10: 97 percent / Me4NBH(OAc)3
11: 87 percent / TsOH*H2O / benzene
12: 98 percent / 2,6-lutidine / CH2Cl2
13: 100 percent / H2 / Pd/C / ethanol; ethyl acetate
14: 83 percent / MgBr2 / diethyl ether
15: 86 percent / (COCl)2, DMSO
16: 1.) NaHMDS / 1.) THF, 2.) THF
17: 88 percent / DIBAL / CH2Cl2
18: 70 percent / t-BuLi, Ti(O-i-Pr)4, MeI / tetrahydrofuran
19: HgCl2 / acetonitrile; tetrahydrofuran
20: DMSO, Ac2O
With
2,6-dimethylpyridine; titanium(IV) isopropylate; N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; pyridine-SO3 complex; hydrogen; trimethylaluminum; tert.-butyl lithium; sodium hexamethyldisilazane; acetic anhydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; mercury dichloride; magnesium bromide; zinc(II) chloride; tetramethylammonium triacetoxyborohydride; methyl iodide;
palladium dihydroxide; palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile; benzene;
DOI:10.1021/ja00153a030