Multi-step reaction with 16 steps
1.1: 96 percent / Sharpless AD-mix-α
2.1: 93 percent / pyridine / CH2Cl2 / 0 °C
3.1: 87 percent / NaN3 / CH2Cl2 / 50 °C
4.1: 97 percent / imidazole / dimethylformamide / 20 °C
5.1: 95 percent / PPh3; H2O / tetrahydrofuran / 20 °C
6.1: 98 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 20 °C
7.1: 82 percent / NBS / dimethylformamide / 20 °C
8.1: 68 percent / NaH / dimethylformamide / 90 °C
9.1: 95 percent / NaBH4 / tetrahydrofuran; methanol / 20 °C
10.1: 92 percent / PPh3; I2; imidazole / tetrahydrofuran / 20 °C
11.1: 98 percent / dimethylformamide / 40 °C
12.1: NaBH4; CoCl2 / methanol / 0 °C
13.1: 67 percent / tetrahydrofuran
14.1: 78 percent / NBS / acetonitrile / 80 °C
15.1: 95 percent / LiOH (3N) / methanol; tetrahydrofuran / 20 °C
16.1: CF3COOH / tetrahydrofuran / 20 °C
16.2: EDC; HOBt / dimethylformamide
With
pyridine; 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; Sharpless AD-mix-α; water; hydrogen; iodine; sodium hydride; triphenylphosphine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
1.1: Addition / 2.1: Tosylation / 3.1: azidation / 4.1: silylation / 5.1: Acetylation / 6.1: Hydrogenolysis / 7.1: Bromination / 8.1: Arylation / 9.1: Reduction / 10.1: Iodination / 11.1: Substitution / 12.1: Reduction / 13.1: Acylation / 14.1: Bromination / 15.1: Hydrolysis / 16.1: Elimination / 16.2: Cyclization;
DOI:10.1016/S0040-4039(99)01430-6