Multi-step reaction with 10 steps
1.1: 82 percent / H2; Et3N / Pd/C / methanol / 192 h / 20 °C / atmospheric pressure
2.1: 68 percent / 1-propanethiol; NaH / dimethylformamide / 20 h / 120 °C
3.1: 87 percent / 2,4,6-collidine / CH2Cl2 / 24 h / 0 °C
4.1: 100 percent / H2; Et3N / Pd/C / methanol / 120 h / 20 °C
5.1: 87 percent / Br2; AcOH / 4 h / 20 °C
6.1: Mg; I2 / tetrahydrofuran / 1.33 h / Heating
6.2: HMPA; CuBr*Me2S / tetrahydrofuran / 2 h / -78 °C
7.1: 638 mg / TBAF / tetrahydrofuran / 0.5 h / 20 °C
8.1: 88 percent / TsOH / xylene / 1 h / Heating
9.1: TESOTf; 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
9.2: 2,6-lutidine; H2O / CH2Cl2 / 0.5 h / 0 °C
10.1: 110 mg / NaBH4 / methanol / 0.17 h / 0 °C
With
2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; 1-thiopropane; tetrabutyl ammonium fluoride; hydrogen; bromine; iodine; triethylsilyl trifluoromethyl sulfonate; sodium hydride; toluene-4-sulfonic acid; magnesium; acetic acid; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; xylene;
DOI:10.1021/ol051570c