Multi-step reaction with 9 steps
1.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C
1.2: 45 percent / tetrahydrofuran / -78 - 20 °C
2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C
2.2: 99 percent / tetrahydrofuran / -78 - 20 °C
3.1: 99 percent / NBS; AgNO3 / dimethylformamide / 3 h / 20 °C
4.1: Zn; dibromoethane; trimethylsilyl chloride / tetrahydrofuran / 3 h / 40 °C
4.2: CuCN; LiCl / tetrahydrofuran / -10 - 0 °C
4.3: 44 percent / tetrahydrofuran / 20 h / -78 °C
5.1: 91 percent / LiBH4 / tetrahydrofuran / 20 h / 20 °C
6.1: 95 percent / imidazole / dimethylformamide / 3 h
7.1: 90 percent / [CpRu(CH3CN)3]PF6 / H2O; acetone / 2 h / 60 °C
8.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
8.2: tetrahydrofuran / 4 h
8.3: 83 percent / Et3N; MsCl / CH2Cl2 / 20 h / 20 °C
9.1: CF3CO2H / CH2Cl2 / 1 h
9.2: 90 percent / K2CO3 / toluene / 68 h / Heating
With
1H-imidazole; N-Bromosuccinimide; lithium borohydride; n-butyllithium; chloro-trimethyl-silane; 1,1-Dibromoethane; silver nitrate; trifluoroacetic acid; lithium hexamethyldisilazane; zinc; lithium diisopropyl amide;
cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol035752n