Multi-step reaction with 13 steps
1.1: Dess-Martin periodinane / CH2Cl2 / 0.75 h / 20 °C
2.1: K2CO3 / methanol / 17 h / 20 °C
3.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / -78 °C
3.2: 42.8 mg / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -78 - 20 °C
4.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C
5.1: 99 percent / Et3N / CH2Cl2 / 3 h / 0 °C
6.1: CuCN / tetrahydrofuran / 0.33 h / 0 °C
6.2: tetrahydrofuran / -78 - 0 °C
7.1: 62.0 mg / N-iodosuccinimide / tetrahydrofuran; acetonitrile / 5 h / 20 °C
8.1: 37.0 mg / Pd2(dba)3; Ph3As; copper(I) thiophene-2-carboxylate / tetrahydrofuran; dimethylsulfoxide / 2 h / 20 °C
9.1: 99 percent / imidazole / dimethylformamide / 1 h / 0 °C
10.1: 75 percent / PPTS / CH2Cl2; methanol / 1 h / 0 °C
11.1: SO3*pyridine; Et3N / CH2Cl2; dimethylsulfoxide / 5 h / 0 °C
12.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
12.2: 11.7 mg / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C
13.1: 77 percent / aq. H2O2; NaHCO3 / tetrahydrofuran / 9 h / 20 °C
With
1H-imidazole; N-iodo-succinimide; n-butyllithium; copper(I) thiophene-2-carboxylate; tris(dibenzylideneacetone)dipalladium (0); pyridine-SO3 complex; triphenyl-arsane; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
8.1: Stille coupling / 12.2: Wittig reaction;
DOI:10.1021/ja066772y