Multi-step reaction with 9 steps
1.1: 92 percent / EtSH; NaH / dimethylformamide / 1 h / 140 °C
2.1: NaH / tetrahydrofuran / 0 - 25 °C
2.2: 93 percent / Bu4NI / tetrahydrofuran / 8 h / 25 °C
3.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C
3.2: 91 percent / tetrahydrofuran / -78 - 0 °C
4.1: aq. NaOH; t-BuOCl / propan-1-ol / 0.08 h / 25 °C
4.2: (DHQ)2PHAL; aq. NaOH; K2OsO2(OH)4 / propan-1-ol / 2 h / 25 °C
4.3: i-Pr2NEt / tetrahydrofuran / 19 h / 30 °C
5.1: H2 / Pd/C / methanol / 3 h
6.1: pyridine / CH2Cl2 / 2 h / 25 °C
7.1: NaH / tetrahydrofuran / 0 - 25 °C
7.2: 69 percent / tetrahydrofuran / 15 h / 25 °C
8.1: H2 / Pd/C / methanol / 1.5 h
9.1: aq. HBF4; t-BuONO / acetonitrile / 0.17 h / 0 °C
9.2: 180 mg / aq. Cu(NO3)2; Cu2O / acetonitrile / 1 h / 0 °C
With
pyridine; sodium hydroxide; tetrafluoroboric acid; n-butyllithium; tert.-butylnitrite; tert-butylhypochlorite; hydrogen; sodium hydride; ethanethiol;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; propan-1-ol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja039795a