Multi-step reaction with 11 steps
1.1: NaHMDS / tetrahydrofuran; dimethylformamide / 2 h / 20 °C
1.2: p-TSOH*H2O / methanol; H2O; tetrahydrofuran / 0.75 h / 20 °C
1.3: 86 percent / 2,6-lutidine / tetrahydrofuran; dimethylformamide / 0.17 h / 0 °C
2.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C / sonication
2.2: H2O2; aq. NaHCO3 / tetrahydrofuran / 1 h / 20 °C
2.3: 99 percent / Dess-Martin periodinane / CH2Cl2 / 0.58 h / 20 °C
3.1: 78 percent / Sc(OTf)3 / benzene / 14 h / 20 °C
4.1: Sc(OTf)3 / CH2Cl2 / 9.5 h / 20 °C
4.2: 92 percent / K2CO3 / methanol / 0.5 h / 20 °C
5.1: 2-nitrobenzeneselenide; Bu3P / tetrahydrofuran / 0.42 h / 20 °C
5.2: 77 percent / H2O2; aq. NaHCO3 / tetrahydrofuran / 3.5 h / 45 °C
6.1: 89 percent / DIBAL-H / CH2Cl2 / 0.5 h / -78 °C
7.1: 76 percent / MeLi / tetrahydrofuran / 1 h / -78 - 20 °C
8.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
9.1: 9 percent / ruthenium ethylidene complex / toluene / 100 °C
10.1: 45 percent / DDQ / CH2Cl2; H2O / 20 °C
11.1: 83 percent / Et3SiH; TMSOTf / CH2Cl2 / 0.33 h / -55 °C
With
triethylsilane; 9-borabicyclo[3.3.1]nonane dimer; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; methyllithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate);
ruthenium ethylidene complex;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.3987/COM-06-S(O)23