Multi-step reaction with 23 steps
1.1: water; potassium hydroxide / tetrahydrofuran; methanol
2.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 20 °C
2.2: 20 °C
3.1: diisobutylaluminium hydride / dichloromethane / -78 °C
4.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate / dichloromethane / -40 °C / Molecular sieve
5.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / 0 °C
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0 °C
7.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C
8.1: potassium tert-butylate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 20 °C
9.1: bis-(1,2-dimethylpropyl)borane / tetrahydrofuran / 0 - 20 °C
9.2: 20 °C
10.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 20 °C
11.1: diethyl ether / -78 °C
12.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 20 °C / Molecular sieve
13.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / diethyl ether / 0 °C
13.2: -78 °C
14.1: Dess-Martin periodane / dichloromethane; tert-butyl alcohol / 20 °C
15.1: pyridinium p-toluenesulfonate / methanol / 80 °C
16.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 20 °C
17.1: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 0 °C
18.1: boron trifluoride tetrahydrofuran complex / tetrahydrofuran / 0 °C
18.2: 0 - 20 °C
19.1: 2,6-dimethylpyridine / dichloromethane / 20 °C
20.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0 °C
21.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0 - 20 °C / Molecular sieve
22.1: toluene-4-sulfonic acid / methanol; dichloromethane / 20 °C
23.1: triethylsilane; trimethylsilyl trifluoromethanesulfonate / propiononitrile / -78 °C
With
2,6-dimethylpyridine; titanium(IV) isopropylate; triethylsilane; tert.-butylhydroperoxide; sodium hypochlorite; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; boron trifluoride tetrahydrofuran complex; diethyl (2R,3R)-tartrate; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; water; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium bromide; potassium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; propiononitrile; tert-butyl alcohol;
2.1: Swern oxidation / 2.2: Wittig reaction / 4.1: Sharpless asymmetric epoxidation / 6.1: Wittig reaction / 11.1: Grignard reaction / 14.1: Dess-Martin oxidation / 17.1: Luche reduction;
DOI:10.1016/j.tetlet.2010.11.127