Multi-step reaction with 15 steps
1: sodium borohydride; nickel(II) chloride hexahydrate / tetrahydrofuran; methanol
2: 84 percent / pyridine / CH2Cl2 / 4 h / 20 °C
3: 96 percent / sodium periodate on silica gel / CH2Cl2 / 4 h
4: CH2Cl2 / 15 h / 20 °C
5: 3.08 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.33 h / 0 °C
6: 94 percent / sodium hydride / tetrahydrofuran / 0 - 20 °C
7: osmium tetroxide; N-methylmorpholine N-oxide / tetrahydrofuran; H2O
8: sodium periodate on silica gel / CH2Cl2 / 2 h
9: 3.00 g / sulfuric acid / tetrahydrofuran / 5 h
10: triethylamine / CH2Cl2 / 2 h
11: 1.79 g / trifluoromethanesulfonic acid / 1 h
12: lithium aluminum hydride / diethyl ether / 0 - 20 °C
13: 0.555 g / triethylamine; 4-dimethylaminopyridine / dioxane / 22 h
14: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h
15: 0.414 g / potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C
With
pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; nickel dichloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water;
4: Diels-Alder reaction;
DOI:10.1021/jo062064j