Multi-step reaction with 12 steps
1.1: diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C
2.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C
2.2: CuCN / diethyl ether; pentane / -78 - -30 °C
2.3: diethyl ether; pentane; tetrahydrofuran / 6 h / -78 °C
3.1: 2,6-lutidine / dimethylformamide / 1 h / 0 °C
3.2: MeI / diethyl ether / 12 h / 20 °C
3.3: 811 mg / K2CO3 / CH2Cl2; methanol; H2O / 3 h / 20 °C
4.1: m-CPBA / CH2Cl2 / 3 h / 20 °C
5.1: NaBH4; CeCl3*7H2O / methanol / 1 h / -78 °C
6.1: imidazole / CH2Cl2 / 0.5 h / 20 °C
7.1: LiEt3BH / tetrahydrofuran / 2 h / 0 °C
7.2: 121 mg / N-methylmorpholine oxide hydrate / TPAP / CH2Cl2 / 1 h / 20 °C
8.1: LiHDMS / tetrahydrofuran / 0.17 h / -78 - -30 °C
8.2: 710 mg / DMPU / tetrahydrofuran / 0.17 h / -78 - -45 °C
9.1: KHMDS / tetrahydrofuran / 0.33 h / -78 °C
9.2: tetrahydrofuran / 0.17 h / -78 °C
10.1: aq. HF / acetonitrile; methanol / 3 h / 0 °C
11.1: 384 mg / NMO*H2O / TPAP / CH2Cl2 / 4 h / 20 °C
12.1: 75 percent / bis(diphenylphosphino)butane; KOAc / Pd2(dba)3*CHCl3 / N,N-dimethyl-acetamide / 12 h / 80 °C
With
1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; bis(diphenylphosphino)butane; hydrogen fluoride; tert.-butyl lithium; potassium acetate; potassium hexamethylsilazane; lithium triethylborohydride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane;
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tetrapropylammonium perruthennate;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetonitrile; pentane;
12.1: Heck cyclization reaction;
DOI:10.1021/ja0650504