Multi-step reaction with 13 steps
1.1: 89 percent / 4-(dimethylamino)pyridine; pyridine / CH2Cl2 / 72 h / 20 °C
2.1: 92 percent / pyridine / tetrahydrofuran / 12 h
3.1: 80 percent / TfOH / CH2Cl2 / 12 h / -78 °C
4.1: 87 percent / dimethylformamide / 60 h / 60 °C
5.1: mercury trifluoroacetate / tetrahydrofuran / 18 h
5.2: 76 percent / NaBH4; NaOH / tetrahydrofuran
6.1: 95 percent / imidazole / dimethylformamide / 72 h
7.1: 90 percent / BCl3 / hexane; CH2Cl2 / 20 h / -78 °C
8.1: 85 percent / pyridinium chlorochromate; molecular sieves / CH2Cl2 / 2 h
9.1: 73 percent / trimethylsilyl triflate / CH2Cl2 / 12 h / -50 °C
10.1: 89 percent / hydrogen / Pd/C / ethyl acetate / 18 h
11.1: 93 percent / DIBAL-H / diethyl ether; hexane / 1 h / -78 °C
12.1: LiHMDS / tetrahydrofuran / 4.5 h / -78 °C
13.1: 82 mg / mercury acetate / tetrahydrofuran; H2O / 0.25 h
With
pyridine; 1H-imidazole; dmap; molecular sieve; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; mercury(II) diacetate; hydrogen; mercury(II) trifluoroacetate; boron trichloride; diisobutylaluminium hydride; pyridinium chlorochromate; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
12.1: wITTIG REACTION;
DOI:10.1021/jo0610412
