Multi-step reaction with 19 steps
1.1: 83 percent / TEA / CH2Cl2 / 0 °C
2.1: 97 percent / Br2; AcOH / CH2Cl2 / 20 °C
3.1: 96 percent / K2CO3 / acetone / Heating
4.1: 97 percent / H2O; NaOH / ethanol / Heating
5.1: 97 percent / (i-Pr)2NEt / CH2Cl2 / 20 °C
6.1: Mg / tetrahydrofuran / 20 °C
6.2: 91 percent / CuI / tetrahydrofuran / 0 - 20 °C
7.1: 96 percent / DMAP / acetonitrile / 20 °C
8.1: 98 percent / TBAF / tetrahydrofuran / 20 °C
9.1: pyridine / CH2Cl2 / 0 °C
10.1: LiN3 / dimethylformamide / 80 °C
11.1: TMSBr / CH2Cl2 / 20 °C
12.1: TFA / CH2Cl2 / 20 °C
13.1: 89 percent / PyHBr3 / CH2Cl2 / 20 °C
14.1: 88 percent / TFA; H2O / 70 °C
15.1: 89 percent / K2CO3 / acetone / Heating
16.1: 87 percent / BCl3 / CH2Cl2 / -78 - 0 °C
17.1: 82 percent / H2 / Rh/C / ethyl acetate / 20 °C
18.1: 92 percent / molecular sieves 4 Angstroem; propylene oxide / acetonitrile / 80 °C
19.1: 80 percent / Pb(OAc)4 / benzene / 80 °C
With
pyridine; lead(IV) acetate; dmap; sodium hydroxide; lithium azide; trimethylsilyl bromide; 4 A molecular sieve; TEA; tetrabutyl ammonium fluoride; water; hydrogen; bromine; boron trichloride; potassium carbonate; magnesium; acetic acid; pyridinium hydrobromide perbromide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; methyloxirane;
Rh on carbon;
In
tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
1.1: Tosylation / 2.1: Bromination / 3.1: Methylation / 4.1: Hydrolysis / 5.1: Etherification / 6.1: Metallation / 6.2: Substitution / 7.1: Substitution / 8.1: Substitution / 9.1: Substitution / 10.1: Substitution / 11.1: Substitution / 12.1: Substitution / 13.1: Bromination / 14.1: Cyclization / 15.1: Methylation / 16.1: Substitution / 17.1: Hydrogenolysis / 18.1: Cyclization / 19.1: Oxidation;
DOI:10.1055/s-1999-3161