Multi-step reaction with 12 steps
1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; tert-butyl alcohol / 20 °C
2: sodium periodate / tetrahydrofuran; water / 1 h / 20 °C
3: toluene / 1.33 h / -78 - 20 °C / Molecular sieve
4: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C
5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 0 - 20 °C / pH 7
6: diethylazodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 2 h / 0 - 20 °C
7: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 °C
8: dmap / toluene / 1.5 h / 20 °C
9: Hoveyda-Grubbs catalyst second generation; p-benzoquinone / toluene / 140 °C
10: palladium 10% on activated carbon; hydrogen / methanol / 25 h / 20 °C
11: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 47 h / 20 °C
12: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 20 °C
With
2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; Hoveyda-Grubbs catalyst second generation; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; p-benzoquinone; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; tert-butyl alcohol;
6: |Mitsunobu Displacement;
DOI:10.1021/ol400408w