Multi-step reaction with 15 steps
1.1: 94 percent / NaOEt / ethanol / 7 h / Heating
2.1: Et3N / CH2Cl2 / 1 h / 20 °C
3.1: NaI / butan-2-one / 2 h / Heating
4.1: NaH / dimethylformamide / 0.5 h
4.2: 86 percent / dimethylformamide / 3 h
5.1: 86 percent / 1 N aq. HCl / methanol / 5 h
6.1: 100 percent / 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C
7.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C
8.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C
9.1: benzene / 1 h / Heating
10.1: benzene / 7 h / Heating
11.1: LiBH4 / tetrahydrofuran / 0.5 h / Heating
12.1: pyridine / 13 h / 20 °C
13.1: Me3SiI / CH2Cl2 / 7 h
13.2: 70 percent / pyridine / 13 h
14.1: 93 percent / 2 M aq. LiOH / tetrahydrofuran; methanol / 2 h / Heating
15.1: aq. KHCO3 / ethyl acetate / 0.25 h / 20 °C
With
pyridine; hydrogenchloride; lithium hydroxide; sodium hydroxide; lithium borohydride; sodium azide; trimethylsilyl iodide; sodium ethanolate; sodium hydride; potassium hydrogencarbonate; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; butanone; benzene;
1.1: Alkylation / 2.1: mesylation / 3.1: Iodination / 4.1: Metallation / 4.2: Alkylation / 5.1: Cyclization / 6.1: Hydrolysis / 7.1: Acylation / 8.1: Substitution / 9.1: Curtius rearrangement / 10.1: Addition / 11.1: Reduction / 12.1: Acetylation / 13.1: demethoxycarbonylation / 13.2: Acetylation / 14.1: Hydrolysis / 15.1: Acylation;
DOI:10.1021/jm000173z