Multi-step reaction with 14 steps
1.1: CrCl2 / tetrahydrofuran; dioxane / 0 °C
2.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl2]; hexamethyltin / 20 °C
2.2: [Pd{P(2-furyl)3}2Cl2]; N-methylpyrrolidinone / 20 °C
3.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C
4.1: 81 percent / 4-pyrrolidinopyridine / CH2Cl2
5.1: 89 percent / lithium hydroxide / H2O; tetrahydrofuran / 0 °C
6.1: 88 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C
7.1: 66 percent / 2,6-lutidine / CH2Cl2 / -20 °C
8.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C
9.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C
10.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C
11.1: 80 percent / dimedone / [Pd(PPh3)4] / tetrahydrofuran / 20 °C
12.1: PhI(OAc)2 / acetonitrile; H2O / 0 °C
13.1: 2,9-dimethyl-1,10-phenanthroline; pyridine / CH2Cl2 / 20 °C
14.1: 61 percent / pyridine*HF / tetrahydrofuran / 50 °C
With
pyridine; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; chromium dichloride; dmap; lithium hydroxide; 2.9-dimethyl-1,10-phenanthroline; [bis(acetoxy)iodo]benzene; hexamethyldistannane; potassium carbonate; dimedone; 4-pyrrolidin-1-ylpyridine; pyridine hydrogenfluoride; lithium tri-t-butoxyaluminum hydride; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/anie.200604053