Multi-step reaction with 14 steps
1.1: NaOH / diethyl ether / 22 h / 20 °C
2.1: 1.91 g / CuCN / tetrahydrofuran / -78 - 0 °C
3.1: 1.36 g / molecular sieves 4 Angstroem; 2,6-di-tert-butylpyridine; AgOTf / CH2Cl2 / 14 h / 0 - 20 °C
4.1: MeOH / KOMe / 3 h
5.1: 1.46 g / TsOH*H2O / acetone / 15 h / 20 °C
6.1: 77 percent / BF3*Et2O / CH2Cl2; pentane / 0.5 h / -20 °C
7.1: 84 percent / MeOH / KOMe / 4 h
8.1: 55 percent / DCC / DMAP / CH2Cl2
9.1: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h
10.1: molecular sieves 4 Angstroem; NaBH3CN; TMSCl / acetonitrile / 0 - 20 °C
10.2: 56.8 mg / DMAP / toluene; CH2Cl2 / 3 h
11.1: DDQ; water / CH2Cl2 / 16 h / 20 °C
12.1: 2,4,6-trichlorobenzoyl chloride; Et3N / toluene / 1.5 h / 20 °C
12.2: 54.6 mg / DMAP / toluene / 2 h
13.1: RuCl2(IMes)(PCy3)=CHPh / CH2Cl2 / 4 h / Heating
14.1: 60 mg / H2 / RhCl(PPh3)3 / ethanol / 760 Torr
With
2,6-dimethylpyridine; methanol; sodium hydroxide; chloro-trimethyl-silane; 2,6-di-tert-butyl-pyridine; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; water; hydrogen; silver trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
dmap; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; RhCl(PPh3)3; boron trifluoride diethyl etherate; potassium methanolate;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetone; toluene; acetonitrile; pentane;
DOI:10.1021/ja068901g