Multi-step reaction with 13 steps
1.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -78 °C
1.2: hexane; tetrahydrofuran; dimethylsulfoxide / -78 - 20 °C
2.1: 995 mg / 2,6-lutidine; NaIO4; OsO4 / dioxane; H2O; 2-methyl-propan-2-ol / 3 h
3.1: 18-crown-6; KHMDS / toluene / 0.75 h / 0 °C
3.2: toluene / 1.92 h / -20 - 0 °C
4.1: DIBAl-H / hexane; CH2Cl2 / 1 h / -78 °C
5.1: MnO2 / CH2Cl2 / 13 h / 20 °C
6.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 - 20 °C
6.2: 243 mg / hexane; tetrahydrofuran / 1 h / -78 - 20 °C
7.1: 83 percent / K2CO3 / methanol / 3 h
8.1: 56 percent / 9-BBN / tetrahydrofuran / 60 h / 45 °C
9.1: 70 percent / Ba(OH)2*8H2O / (dppf)PdCl2 / dimethylformamide / 2 h / 20 °C
10.1: 78 percent / N-(3-dimethylaminopropyl)-N'-ethyl-carbodiimide*HCl; 4-pyrrolidino-pyridine / CH2Cl2 / 96 h / 20 °C
11.1: 78 percent / Grubbs second generation catalyst / CH2Cl2 / 72 h / 20 °C
12.1: TBAF / tetrahydrofuran / 36 h / 0 - 20 °C
13.1: 1-hydroxy-benzotriazole; N-methylmorpholine; N-3-(dimethylaminopropyl)-N'-ethyl-carbodiimide*HCl / CH2Cl2 / 20 h / 0 - 20 °C
With
4-methyl-morpholine; 2,6-dimethylpyridine; manganese(IV) oxide; barium dihydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; 4-pyrrolidin-1-ylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 9-borabicyclo[3.3.1]nonane dimer;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
3.1: Still-Gennari olefination / 3.2: Still-Gennari olefination / 6.2: Wittig olefination / 9.1: Suzuki reaction;
DOI:10.1021/ja072334v