Multi-step reaction with 10 steps
1.1: ozone / dichloromethane / -78 °C / Inert atmosphere
1.2: 4 h / -78 - 20 °C / Inert atmosphere
2.1: triethylamine; (-)-diisopinocamphenylborane chloride / diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere
2.2: 17 h / -78 - -20 °C / Inert atmosphere
3.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 21 h / -30 - -20 °C / Inert atmosphere
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / Molecular sieve; Inert atmosphere
5.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
6.1: dimethyl sulfide borane / toluene / 3 h / 100 °C / Inert atmosphere
7.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere
8.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
9.1: pyridine; pyridine hydrofluoride / tetrahydrofuran / 7 h / 20 °C / Inert atmosphere
10.1: trityl tetrafluoroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
With
pyridine; 2,6-dimethylpyridine; carbon tetrabromide; pyridine hydrofluoride; trityl tetrafluoroborate; dimethyl sulfide borane; Dess-Martin periodane; ozone; acetic acid; triethylamine; triphenylphosphine; (-)-diisopinocamphenylborane chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile;
2.1: Aldol condensation / 2.2: Aldol condensation / 7.1: Dess-Martin oxidation;
DOI:10.1039/c2ob25100k