Multi-step reaction with 17 steps
1.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; cyclohexane / 0.75 h / -78 °C / Inert atmosphere
1.2: 2 h / -78 °C / Inert atmosphere
2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
4.1: [bis(acetoxy)iodo]benzene; potassium hydrogencarbonate / 0.5 h / 0 - 23 °C / Inert atmosphere
5.1: Trimethyl borate / toluene / 16.3 h / 23 °C / Inert atmosphere; Reflux
6.1: palladium 10% on activated carbon; hydrogen / methanol / 0.5 h / 23 °C
7.1: pyridinium chlorochromate / dichloromethane / 16 h / 23 °C / Inert atmosphere; Molecular sieve
8.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 - 0 °C / Inert atmosphere
9.1: bis-triphenylphosphine-palladium(II) chloride; formic acid; tributyl-amine / N,N-dimethyl-formamide / 16 h / 23 - 78 °C / Inert atmosphere
10.1: methanol; samarium diiodide / tetrahydrofuran / 0.33 h / 23 °C / Inert atmosphere
11.1: tetrahydrofuran / 0.5 h / 0 - 23 °C / Inert atmosphere
12.1: tert.-butylhydroperoxide / decane; ethyl acetate / 0.5 h / 23 °C / Inert atmosphere; Molecular sieve
12.2: 16 h / 23 °C / Inert atmosphere
13.1: Martins sulfurane / dichloromethane / 2 h / 23 °C / Inert atmosphere
14.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
14.2: 3 h / -78 - 0 °C / Inert atmosphere
15.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 0.25 h / 23 °C / Inert atmosphere
15.2: 0.33 h / 23 °C / Inert atmosphere
16.1: methanol; water; lithium hydroxide / 5 h / 23 - 50 °C
17.1: triethylamine; HATU / N,N-dimethyl-formamide / 14 h / 23 °C / Inert atmosphere
With
methanol; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; bis-triphenylphosphine-palladium(II) chloride; formic acid; samarium diiodide; Martins sulfurane; Trimethyl borate; tributyl-amine; N,N,N,N,-tetramethylethylenediamine; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; sec.-butyllithium; potassium hexamethylsilazane; potassium hydrogencarbonate; triethylamine; HATU; pyridinium chlorochromate; lithium hydroxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole;
In
tetrahydrofuran; methanol; diethyl ether; decane; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
2.1: Corey-Bakshi-Shibata reduction / 5.1: Intramolecular Diels-Alder reaction;
DOI:10.1002/ejoc.201001281