Multi-step reaction with 9 steps
1: sodium dihydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 40 °C / Inert atmosphere
2: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere
3: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
4: sodium periodate; rhodium(III) chloride hydrate / acetonitrile; water / 5 h / 20 °C / Inert atmosphere
5: (1S)-10-camphorsulfonic acid / ethanol / 27 h / 0 °C / Inert atmosphere
6: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere
7: boron trifluoride diethyl etherate / dichloromethane / 2.5 h / -40 °C / Inert atmosphere
8: diethyl methoxy borane; sodium tetrahydroborate / methanol; tetrahydrofuran / 3 h / -30 °C / Inert atmosphere
9: (1S)-10-camphorsulfonic acid / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; rhodium(III) chloride hydrate; diethyl methoxy borane; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
1: |Baeyer-Villiger Ketone Oxidation / 7: |Mukaiyama Aldol Addition;
DOI:10.1002/chem.201304297