Multi-step reaction with 14 steps
1.1: MP-TsOH / ethanol; water / 82 °C
2.1: zinc trifluoromethanesulfonate / ethanol / 100 °C / Schlenk technique
3.1: methyl p-toluene sulfonate / toluene / 40 °C
4.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C
5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / tetrahydrofuran / 20 °C
6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone; water / 20 °C
7.1: lead(IV) tetraacetate / toluene / 20 °C
8.1: triethylamine; dicyclohexylboron chloride / diethyl ether / 2 h / 0 °C
8.2: 2 h / -78 °C
9.1: pyridinium p-toluenesulfonate / methanol / 20 °C
10.1: 2,6-dimethylpyridine / tetrahydrofuran / -78 °C
11.1: cerium(III) chloride / -78 °C
12.1: triethylamine; dicyclohexylboron chloride / diethyl ether / -55 °C
12.2: -70 °C
13.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
14.1: zinc; lead(II) iodide; chloro-trimethyl-silane / 0 - 20 °C
14.2: 20 °C
14.3: 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; osmium(VIII) oxide; chloro-trimethyl-silane; cerium(III) chloride; lithium hydroxide monohydrate; dicyclohexylboron chloride; lead(IV) tetraacetate; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; benzotriazol-1-ol; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; methyl p-toluene sulfonate; lead(II) iodide; zinc;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1039/c3sc50304f