Multi-step reaction with 8 steps
1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 20 °C
1.2: 20 °C
2.1: diisobutylaluminium hydride / dichloromethane / -78 °C
3.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate / dichloromethane / -40 °C / Molecular sieve
4.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / 0 °C
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0 °C
6.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C
7.1: potassium tert-butylate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 20 °C
8.1: bis-(1,2-dimethylpropyl)borane / tetrahydrofuran / 0 - 20 °C
8.2: 20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hypochlorite; oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diethyl (2R,3R)-tartrate; potassium tert-butylate; water; sodium hexamethyldisilazane; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium bromide;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
1.1: Swern oxidation / 1.2: Wittig reaction / 3.1: Sharpless asymmetric epoxidation / 5.1: Wittig reaction;
DOI:10.1016/j.tetlet.2010.11.127