Multi-step reaction with 13 steps
1.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere
1.2: 0.17 h / -78 - 0 °C / Inert atmosphere
2.1: tert.-butyl lithium / diethyl ether; pentane / 1.5 h / -78 °C / Inert atmosphere
2.2: -78 - 25 °C / Inert atmosphere
2.3: 4 h / 20 - 25 °C / Inert atmosphere
3.1: water; acetic acid / tetrahydrofuran / 5 h / 50 °C / Inert atmosphere
4.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere
4.2: 1 h / -78 - 0 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran; hexane / 2.33 h / -78 °C / Inert atmosphere
5.2: 4 h / -78 - 0 °C / Inert atmosphere
5.3: Inert atmosphere
6.1: 1H-imidazole / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
7.2: 2 h / -78 °C / Inert atmosphere
8.1: potassium osmate(VI) dihydrate; methanesulfonamide; water; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) / tert-butyl alcohol / 60 h / 0 °C / Inert atmosphere
9.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 48 h / 35 °C / Inert atmosphere
10.1: 10-camphorsufonic acid / dichloromethane / 1.5 h / 20 - 25 °C / Inert atmosphere
11.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 12.17 h / 0 - 40 °C / Inert atmosphere
12.1: methanol; potassium carbonate / 0 °C / Inert atmosphere
13.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1.17 h / 0 - 25 °C / Inert atmosphere
With
1H-imidazole; methanol; dmap; potassium osmate(VI) dihydrate; n-butyllithium; zirconocene dichloride; methanesulfonamide; 10-camphorsufonic acid; water; iodine; tert.-butyl lithium; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol; pentane;
8.1: Sharpless dihydroxylation / 9.1: Parikh-Doering oxidation;
DOI:10.1021/ol203342e