Multi-step reaction with 16 steps
1: tetrabutylammoniun azide / toluene / 20 °C
2: trifluoroacetic acid / acetonitrile; water / 0 - 20 °C
3: Dess-Martin periodane / dichloromethane / 0 - 20 °C
4: tetrahydrofuran / -78 °C
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C
6: zinc trifluoromethanesulfonate; acetic acid / 80 °C
7: potassium carbonate / methanol / 20 °C
8: triethylamine; dmap / 0 - 20 °C
9: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 - 0 °C
10: ytterbium(III) triflate / toluene / 80 °C
11: sodium cyanoborohydride; acetic acid / toluene / 12 h / 40 °C / Inert atmosphere
12: pyrographite; triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
13: 4-methylmorpholine N-oxide; osmium(VIII) oxide; water / acetone; tetrahydrofuran / 2 h / 20 °C
14: sodium periodate / water; tetrahydrofuran / 3 h / 20 °C
15: trifluoroacetic acid / neat (no solvent) / 40 °C
16: ammonium chloride; zinc / water; tetrahydrofuran; ethanol / 6 h / 20 °C
With
pyridine; dmap; sodium periodate; osmium(VIII) oxide; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; water; tetrabutylammoniun azide; zinc trifluoromethanesulfonate; sodium cyanoborohydride; potassium carbonate; pyrographite; ammonium chloride; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; ytterbium(III) triflate; zinc;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; acetonitrile;
DOI:10.1021/jo301638z