Multi-step reaction with 11 steps
1: 100 percent / pyridine / CH2Cl2 / 0.5 h / 0 °C
2: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C
3: 100 percent / Pd(PPh3)4 / acetonitrile / 2 h / 20 °C
4: 100 percent / aq. OsO4; NMO / tetrahydrofuran / 20 h / 20 °C
5: 96 percent / aq. NaIO4 / tetrahydrofuran / 1 h / 20 °C
6: 72 percent / tetrahydrofuran / 0.5 h / 0 °C
7: 100 percent / TPAP; NMO; 4 Angstroem MS / CH2Cl2 / 1 h / 20 °C
8: 100 percent / NaH / tetrahydrofuran / 3 h / 80 °C
9: 100 percent / H2 / 10 percent Pd/C / ethyl acetate / 4 h / 20 °C
10: 100 percent / DIBALH / CH2Cl2; hexane / 0.33 h / -78 °C
11: 80 percent / DDQ / dioxane / 0.67 h / 20 °C
With
pyridine; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; ethyl acetate; acetonitrile;
1: Esterification / 2: desilylation / 3: Cyclization / 4: Oxidation / 5: Oxidation / 6: Grignard reaction / 7: Oxidation / 8: Wadsworth-Emmons reaction / 9: Catalytic hydrogenation / 10: Reduction / 11: Oxidation;
DOI:10.3987/com-99-8839