Multi-step reaction with 11 steps
1: 18 percent / pyridine / 2 h
2: 96 percent / sodium methoxide / methanol / 0.25 h / 20 °C
3: pyridine / CH2Cl2 / 1 h / 4 °C
4: 0.80 g / tetrabutylammonium fluoride / tetrahydrofuran / 24 h / 4 °C
5: 82 percent / hydrochloric acid / dioxane / 48 h / Heating
6: 70 percent / NaBH4 / methanol / 1.5 h / 20 °C
7: 87 percent / pyridine / 20 °C
8: 79 percent / oxalyl chloride; dimethyl sulfoxide; diisopropylethylamine / CH2Cl2 / 0.17 h
9: 87 percent / p-toluenesulfonic acid monohydrate / benzene / 18 h / Heating
10: 97 percent / sodium methoxide / methanol / 9 h / -10 °C
11: 90 percent / 2,6-lutidine; tellurium tetrachloride / CH2Cl2 / 1 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium methylate; tellurium tetrachloride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; benzene;
8: Swern oxidation;
DOI:10.1021/ol048459b