Multi-step reaction with 15 steps
1.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere
2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 12 h / 20 °C / Inert atmosphere
3.1: methanol; L-diisopinocampheylborane / diethyl ether / 1 h / 0 - 20 °C
3.2: 3 h / -70 °C
4.1: potassium carbonate / methanol
5.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate / dichloromethane / -70 - 0 °C / Molecular sieve
6.1: 1H-imidazole; dmap / dichloromethane / 2 h / 20 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -70 °C
7.2: 2 h / -70 - 20 °C
8.1: dimethyl zinc(II); tert.-butyl lithium / tetrahydrofuran; n-heptane; pentane / 1.75 h / -70 °C / Inert atmosphere
8.2: 3 h / -70 °C / Inert atmosphere
9.1: pyridinium p-toluenesulfonate / tetrahydrofuran; methanol
10.1: pyridinium p-toluenesulfonate
11.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / Reflux; Inert atmosphere
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C
13.1: quinoline; hydrogen / hexane; ethyl acetate / 1.5 h
14.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.25 h / 0 °C
15.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C
15.2: 2 h / 0 °C
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; quinoline; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; dmap; oxalyl dichloride; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; hydrogen; dimethyl zinc(II); tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; L-diisopinocampheylborane;
In
tetrahydrofuran; methanol; diethyl ether; hexane; n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil; pentane;
5.1: Sharpless epoxidation / 7.1: Swern oxidation / 7.2: Swern oxidation / 8.2: Felkin-Anh addition;
DOI:10.1021/ol201920j