Multi-step reaction with 16 steps
1.1: 80 percent / KBH(s-Bu)3 / tetrahydrofuran; ethanol / -78 °C
2.1: n-Bu3P / tetrahydrofuran / 20 °C
3.1: H2O2 / tetrahydrofuran; H2O / 0 - 20 °C
4.1: dimethylformamide; tetrahydrofuran / 0 °C
5.1: 96 percent / (PCy3)2Cl2Ru=CHPh / CH2Cl2 / 20 °C
6.1: TFA / tetrahydrofuran / 20 °C
6.2: 98 percent / imidazole / dimethylformamide / 20 °C
7.1: m-CPBA; NaHCO3 / CH2Cl2 / 0 - 20 °C
8.1: LiAlH4 / diethyl ether / -20 °C
9.1: TBAI; NaH / tetrahydrofuran; dimethylformamide / 20 °C
9.2: 51 percent / CSA / methanol; tetrahydrofuran / 0 °C
10.1: 95 percent / iodine; PPh3; imidazole / tetrahydrofuran / 20 °C
11.1: 90 percent / dimethylsulfoxide / 45 °C
12.1: DIBAL-H / CH2Cl2 / -95 °C
12.2: 83 percent / NaBH4 / CH2Cl2; methanol / -20 - 20 °C
13.1: 95 percent / nBu3P; pyridine / 20 °C
14.1: NCS / CH2Cl2; CCl4 / 20 °C
15.1: 70 percent / AgOTf; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem MS / CH2Cl2; CCl4 / -90 - -15 °C
16.1: 93 percent / AgOTf; i-Pr2NEt; 4 Angstroem MS / benzene / 20 °C
With
pyridine; 1H-imidazole; N-chloro-succinimide; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; tributylphosphine; 4 Angstroem MS; dihydrogen peroxide; iodine; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium tri-sec-butyl-borohydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic acid;
Grubbs catalyst first generation;
In
tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.tetlet.2007.01.102