Multi-step reaction with 12 steps
1.1: triethylamine / diethyl ether / 2 h / 0 °C / Inert atmosphere
2.1: diethyl ether / 11 h / -78 - -20 °C / Inert atmosphere
2.2: 1.5 h / 0 °C / pH 7 / aq. buffer
3.1: samarium diiodide / tetrahydrofuran / 2 h / -10 °C / Inert atmosphere
4.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
5.1: 10% Pd(OH)2 on C; hydrogen / tetrahydrofuran / 3 h / 20 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
6.2: 0.5 h / -78 - 0 °C / Inert atmosphere
7.1: diethyl ether / 18 h / -78 - -20 °C / Inert atmosphere
7.2: 1 h / 0 °C / pH 7 / aq. buffer
8.1: sodium tetrahydroborate / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere
8.2: 20 °C / pH 7 / aq. buffer
9.1: methanol; potassium carbonate / 2 h / 20 °C / Inert atmosphere
10.1: lead(IV) tetraacetate; sodium carbonate / dichloromethane / 1 h / 0 °C / Inert atmosphere
11.1: potassium carbonate / methanol / 16 h / 20 °C / Inert atmosphere
12.1: bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
12.2: 1 h / 20 °C / Inert atmosphere
With
1H-imidazole; methanol; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; samarium diiodide; oxalyl dichloride; 10% Pd(OH)2 on C; hydrogen; tri-n-butyl-tin hydride; lead(IV) tetraacetate; sodium carbonate; potassium carbonate; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
2.1: Aldol reaction / 3.1: Evans-Tishchenko reduction / 6.1: Swern oxidation / 6.2: Swern oxidation / 7.1: Aldol reaction / 11.1: Ohira-Bestmann alkynation / 12.2: Liebeskind-Stille coupling;
DOI:10.1016/j.tet.2011.09.012