Multi-step reaction with 8 steps
1.1: platinum(IV) oxide; hydrogen / ethyl acetate / 2.25 h / 20 °C / 760.05 Torr
1.2: 1 h / 80 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C
2.2: 4 h / 0 - 20 °C
3.1: sodium ethanolate / N,N-dimethyl-formamide / 21 h / 120 °C
4.1: (S)-2,2’-bis-[(4S)-(-iso-butyl)-4,5-dihydrooxazol-2-yl]-1,1’-binaphthalene; palladium(II) trifluoroacetate; p-benzoquinone / methanol / 24 h / 20 °C
5.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 - 20 °C
6.1: ortho-nitrophenyl selenocyanate; tributylphosphine / tetrahydrofuran / 4 h / 0 °C
6.2: 4 h / -40 °C
6.3: 15 h / -40 °C
7.1: potassium osmate(VI) dihydrate; (DHQ)2-AQN; potassium hexacyanoferrate(III); potassium carbonate / tert-butyl alcohol; water / 72 h / 20 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / 0 °C
With
2,6-dimethylpyridine; platinum(IV) oxide; potassium osmate(VI) dihydrate; lithium aluminium tetrahydride; n-butyllithium; ortho-nitrophenyl selenocyanate; palladium(II) trifluoroacetate; tributylphosphine; potassium hexacyanoferrate(III); (S)-2,2’-bis-[(4S)-(-iso-butyl)-4,5-dihydrooxazol-2-yl]-1,1’-binaphthalene; (DHQ)2-AQN; hydrogen; sodium ethanolate; potassium carbonate; p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/chem.201402495