Multi-step reaction with 12 steps
1.1: 66 percent / diethyl zinc / toluene; hexane / 0.5 h / 0 °C
2.1: 77 percent / Dess-Martin periodinane / CH2Cl2 / 12 h / 20 °C
3.1: 84 percent / H2 / Pd(OH)2 / ethanol / 0.5 h / 20 °C
4.1: pyridine / CH2Cl2 / 2 h / -45 °C
5.1: 0.742 g / TBAF; AcOH / tetrahydrofuran / 2.5 h / 20 °C
6.1: 86 percent / pyridinium p-toluenesulfonate / benzene / 1 h / Heating
7.1: 100 percent / K2CO3 / tetrahydrofuran; methanol / 1 h / 20 °C
8.1: 100 percent / SmI2; methanol / tetrahydrofuran; hexamethylphosphoric acid triamide / 5 h / 20 °C
9.1: TBAF; 2,6-di-t-butyl-4-hydroxytoluene / tetrahydrofuran / 3 h / 20 °C
9.2: 45 percent / sodium methoxide / methanol; tetrahydrofuran / 60 h / 20 °C
10.1: pyridine / CH2Cl2 / 0.25 h / 20 °C
11.1: 2,6-lutidine / CH2Cl2 / 12 h / -45 °C
12.1: 6.6 mg / aq. hydrogen peroxide; aq. Na2CO3 / ethyl acetate / 1 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; methanol; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; diethylzinc; 2,6-di-tert-butyl-4-hydroxytoluene; pyridinium p-toluenesulfonate; sodium carbonate; potassium carbonate; Dess-Martin periodane; acetic acid;
palladium dihydroxide;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; ethyl acetate; toluene; benzene;
1.1: Cycloaddition / 2.1: Dess-Martin oxidation / 3.1: Hydrogenolysis / 4.1: cyclocondensation / 5.1: desilylation / 6.1: cyclocondensation / 7.1: Ring cleavage / 8.1: Ring cleavage / 9.1: desilylation / 9.2: Isomerization / 10.1: cyclocondensation / 11.1: silylation / 12.1: Ring cleavage;
DOI:10.1021/ja9939439