Multi-step reaction with 11 steps
1.1: 86 percent / pyridinium p-toluenesulfonate / benzene / 1 h / Heating
2.1: 100 percent / K2CO3 / tetrahydrofuran; methanol / 1 h / 20 °C
3.1: 100 percent / SmI2; methanol / tetrahydrofuran; hexamethylphosphoric acid triamide / 5 h / 20 °C
4.1: TBAF; 2,6-di-t-butyl-4-hydroxytoluene / tetrahydrofuran / 3 h / 20 °C
4.2: 45 percent / sodium methoxide / methanol; tetrahydrofuran / 60 h / 20 °C
5.1: pyridine / CH2Cl2 / 0.25 h / 20 °C
6.1: 2,6-lutidine / CH2Cl2 / 12 h / -45 °C
7.1: 6.6 mg / aq. hydrogen peroxide; aq. Na2CO3 / ethyl acetate / 1 h / 20 °C
8.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
9.1: 97 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 0.08 h / 20 °C
10.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C
10.2: 89 percent / tetrahydrofuran / 1 h / -78 °C
11.1: 91 percent / tetrakis(triphenylphosphine)palladium / diethyl ether; tetrahydrofuran / 1 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; methanol; samarium diiodide; tetrabutyl ammonium fluoride; dihydrogen peroxide; 2,6-di-tert-butyl-4-hydroxytoluene; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium carbonate; potassium carbonate; Dess-Martin periodane;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; ethyl acetate; benzene;
1.1: cyclocondensation / 2.1: Ring cleavage / 3.1: Ring cleavage / 4.1: desilylation / 4.2: Isomerization / 5.1: cyclocondensation / 6.1: silylation / 7.1: Ring cleavage / 8.1: Dess-Martin oxidation / 9.1: Addition / 10.1: Metallation / 10.2: Condensation / 11.1: Condensation;
DOI:10.1021/ja9939439