Multi-step reaction with 12 steps
1.1: ozone / dichloromethane / -78 °C
1.2: -78 - 20 °C
2.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / diethyl ether / 0 °C
2.2: -78 °C
3.1: Dess-Martin periodane / dichloromethane; tert-butyl alcohol / 20 °C
4.1: pyridinium p-toluenesulfonate / methanol / 80 °C
5.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 20 °C
6.1: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 0 °C
7.1: boron trifluoride tetrahydrofuran complex / tetrahydrofuran / 0 °C
7.2: 0 - 20 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 20 °C
9.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0 °C
10.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0 - 20 °C / Molecular sieve
11.1: toluene-4-sulfonic acid / methanol; dichloromethane / 20 °C
12.1: triethylsilane; trimethylsilyl trifluoromethanesulfonate / propiononitrile / -78 °C
With
2,6-dimethylpyridine; triethylsilane; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; boron trifluoride tetrahydrofuran complex; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; water; pyridinium p-toluenesulfonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; propiononitrile; tert-butyl alcohol;
3.1: Dess-Martin oxidation / 6.1: Luche reduction;
DOI:10.1016/j.tetlet.2010.11.127