Multi-step reaction with 12 steps
1.1: mol. sieves / hexane; CH2Cl2 / 90 h / 23 °C
1.2: 71 percent / AgOTf / CH2Cl2 / 1.5 h / 0 °C
2.1: 91 percent / LiAlH4 / tetrahydrofuran / 2 h / -78 °C
3.1: 93 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 0 °C
4.1: BuMgCl / tetrahydrofuran / 0.5 h / 0 - 23 °C
4.2: tetrahydrofuran / 1 h / 0 - 23 °C
5.1: Et3N / CH2Cl2 / 0.5 h / 0 °C
5.2: 2.34 g / HCO2NH4; Bu3P / [Pd2(dba)3] / benzene / 48 h / 23 °C
6.1: 95 percent / quinoline; H2 / Pd/BaSO4 / methanol / 5 h / 23 °C
7.1: Ba(OH)2; H2O / dioxane / 2 h / 100 °C
8.1: 1.43 g / NaOH / tetrahydrofuran; H2O / 6 h / 23 °C
9.1: Et3N / CH2Cl2 / 0.5 h / 0 °C
10.1: 285 mg / H2SO4 / dioxane / 0.25 h / 23 °C
11.1: H2 / Raney-Ni / ethanol / 36 h / 23 °C
12.1: 119 mg / tetrahydrofuran / 2 h / 0 - 23 °C
With
quinoline; barium dihydroxide; sodium hydroxide; lithium aluminium tetrahydride; molecular sieve; oxalyl dichloride; sulfuric acid; water; hydrogen; butyl magnesium bromide; dimethyl sulfoxide; triethylamine;
Pd-BaSO4; nickel;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water;
1.1: Cycloaddition / 1.2: Isomerization / 2.1: Reduction / 3.1: Swern oxidation / 4.1: Metallation / 4.2: Grignard reaction / 5.1: mesylation / 5.2: Hydrogenolysis / 6.1: Catalytic hydrogenation / 7.1: Decarboxylation / 8.1: Acylation / 9.1: mesylation / 10.1: Cyclization / 11.1: Reduction / 12.1: Acylation;
DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5