Multi-step reaction with 11 steps
1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - -10 °C / Inert atmosphere
2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere
3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 °C / Inert atmosphere
4.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere
5.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water; tert-butyl alcohol / 20 - 25 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.33 h / 20 - 25 °C / Inert atmosphere
6.2: 20 h / 20 - 25 °C / Inert atmosphere
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.17 h / 20 - 25 °C / pH 7.1 / Inert atmosphere; aq. phosphate buffer
8.1: dmap / toluene / 8 h / 0 - 60 °C / Inert atmosphere
9.1: diethylamine / acetonitrile / 1 h / 0 - 20 °C / Inert atmosphere
10.1: 1-hydroxy-7-aza-benzotriazole; HATU / N,N-dimethyl-formamide / 14 h / 0 - 20 °C / Inert atmosphere
11.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; boron trifluoride diethyl etherate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; diethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride;
In
1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;
6.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1039/c2cc34187e