Multi-step reaction with 10 steps
1.1: tetramethylammonium triacetoxyborohydride / acetone; acetic acid / 30 h / -20 °C
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 0 °C / Molecular sieve
3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
3.2: 0.5 h / -78 °C
3.3: 0.08 h / -78 °C
4.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 0.5 h / 120 °C
5.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C
6.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve
7.1: potassium tert-butylate / diethyl ether / 0.5 h / 0 - 20 °C
7.2: 0.5 h / 0 °C
8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform; water / 0.5 h / 0 °C
9.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 5 h / 0 - 20 °C
10.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; methanesulfonamide / 1,4-dioxane / 4 h / 0 - 20 °C
With
dmap; osmium(VIII) oxide; tetrapropylammonium perruthennate; 2,2'-azobis(isobutyronitrile); methanesulfonamide; potassium tert-butylate; water; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; chloroform; water; acetic acid; acetone; toluene;
6.1: |Ley Oxidation / 7.1: |Wittig Olefination / 7.2: |Wittig Olefination;
DOI:10.1016/j.tetasy.2013.07.012