Multi-step reaction with 13 steps
1.1: Dess-Martin periodane / dichloromethane / 3 h / Inert atmosphere
2.1: toluene / 16 h / -78 °C / Molecular sieve; Inert atmosphere
3.1: dmap; triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4.1: ozone; triphenylphosphine / dichloromethane / -78 - 20 °C / Inert atmosphere
5.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
5.2: 2 h / -78 °C / Inert atmosphere
6.1: pyridinium p-toluenesulfonate / acetone / 12 h / 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
8.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
9.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
9.2: 2 h / -78 °C / Inert atmosphere
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
11.1: dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide / dichloromethane / 15 h / 30 °C
12.1: 1H-imidazole; dmap / dichloromethane / 15 h / 40 °C / Inert atmosphere
13.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / Inert atmosphere; Reflux
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; Dess-Martin periodane; ozone; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; pentane;
1.1: Dess-Martin oxidation;
DOI:10.1021/ol2007296