Multi-step reaction with 10 steps
1.1: Nitrosobenzene; L-proline / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere
1.2: 6 h / 0 °C / Inert atmosphere
2.1: dmap; 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere
5.1: camphorsulphonic acid / dichloromethane / 20 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / dichloromethane / 2.5 h / -78 °C / Inert atmosphere
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
7.2: 1 h / 20 °C / Inert atmosphere
8.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Inert atmosphere; Reflux
9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C / Inert atmosphere
10.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; dmap; osmium(VIII) oxide; Hoveyda-Grubbs catalyst second generation; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; Nitrosobenzene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; lithium hexamethyldisilazane;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;
3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination / 7.1: |Wittig Olefination / 7.2: |Wittig Olefination / 8.1: |Cross Metathesis;
DOI:10.1016/j.tet.2014.02.072