Multi-step reaction with 13 steps
1: 100 percent / HCl / 6 h / 60 °C
2: 74 percent / Et3N / dimethylformamide / 16 h / 20 °C
3: 83 percent / CH2Cl2 / 120 h / 20 °C
4: 93 percent / Bu3SnH; AIBN / toluene / 2 h / 85 °C
5: 80 percent / pyridine; POCl3 / 10 h / 20 °C
6: 84 percent / TBAF / tetrahydrofuran / 15 h / 0 °C
7: 98 percent / diisopropyl azodicarboxylate; PPh3 / tetrahydrofuran / 2 h / 20 °C
8: 85 percent / aq. HCl / methanol / 2 h / 20 °C
9: 85 percent / diisopropyl azodicarboxylate; PPh3 / tetrahydrofuran / 2 h / 20 °C
10: 75 percent / NaOMe / methanol / 20 °C
11: 96 percent / imidazole / CH2Cl2 / 2 h / 20 °C
12: 97 percent / DIBAL-H / toluene / 2 h / -78 °C
13: 100 percent / PCC / CH2Cl2 / 2 h / 20 °C
With
pyridine; 1H-imidazole; hydrogenchloride; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; pyridinium chlorochromate; trichlorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
1: Methylation / 2: silylation / 3: thioacylation / 4: dethiocarboxylation / 5: Dehydration / 6: Dehydration / 7: Esterification / 8: Hydrolysis / 9: Esterification / 10: ester cleavage / 11: Condensation / 12: Reduction / 13: Oxidation;
DOI:10.1021/jo000443l