Multi-step reaction with 10 steps
1.1: 47 percent / K2CO3 / acetone / 24 h / Heating
2.1: 64 percent / imidazole / dimethylformamide / 0 - 20 °C
3.1: H2 / tetrahydrofuran / 18 h
4.1: NaHCO3 / tetrahydrofuran / 0 - 20 °C
5.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -78 °C
5.2: tetrahydrofuran / -78 - 20 °C
6.1: NEt3 / CH2Cl2 / 4 h / 20 °C
7.1: NaN3 / dimethylformamide / 65 °C
8.1: H2 / Pd/C / methanol; tetrahydrofuran / 24 h / 760.05 Torr
9.1: pyridine / CH2Cl2 / 20 °C
10.1: 1.27 g / AcOH; THF / H2O / 16 h / 20 °C
With
tetrahydrofuran; pyridine; 1H-imidazole; sodium azide; hydrogen; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
1.1: Substitution / 2.1: silylation / 3.1: Reduction / 4.1: Acylation / 5.1: Metallation / 5.2: Ring cleavage / 6.1: mesylation / 7.1: Substitution / 8.1: Reduction / 9.1: Acetylation / 10.1: desilylation;
DOI:10.1021/jm990373e