Multi-step reaction with 12 steps
1: 40percent aqueous KOH / ethanol / 2 h / 120 °C
2: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / -20 °C
3: Jones reagent / acetone / 0.5 h / 0 °C
4: 1.) cupric acetate monohydrate 2.) lead tetraacetate / pyridine / 1.) 0.5 h, room temperature 2a.) 1 h, 23 deg C 2b.) 2 h, 80 deg C
5: LDA / 1.) -78 deg C, 1 h 2.) -40 deg C, 2 h
6: anhydrous zinc chloride
7: 1.) ozone 2.) Me2S / 1.) CH2Cl2, -78 deg C 2.) 23 deg, 26 h
8: 1.) Jones reagent 2.) CH2N2 / 1a.) acetone, -10 deg C, 20 min 1b.) -5 deg C
9: 96 percent / H2 / Pd/C / ethyl acetate; hexane / 0.25 h / 1034.3 Torr
10: 76 percent / imidazole / dimethylformamide / 2 h / 23 °C
11: 54 percent / KS-Selectride / tetrahydrofuran / 0 °C
12: 83 percent / 4-(dimethylamino)pyridine, Me2N-CH2-CH2-NH2 / CH2Cl2; pyridine / 18 h / 23 °C
With
diazomethane; 1H-imidazole; lead(IV) acetate; dmap; potassium hydroxide; jones reagent; potassium trisiamylborohydride; dimethylsulfide; hydrogen; copper diacetate; ozone; N,N-dimethylethylenediamine; triphenylphosphine; zinc(II) chloride; lithium diisopropyl amide; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00179a018
