Multi-step reaction with 10 steps
1.1: 42 percent / NaI / 18 h / 85 °C
2.1: NEt3; PPh3 / Pd(OAc)2 / dimethylformamide / 20 h / 40 °C
3.1: NH3 / methanol / 0.25 h / 20 °C
4.1: 66 percent / PCC / CH2Cl2 / 24 h / 40 °C
5.1: n-BuLi / tetrahydrofuran; hexane / 0 °C
5.2: 83 percent / tetrahydrofuran; hexane / 18 h / Heating
6.1: 78 percent / NaH / tetrahydrofuran / 4.5 h / 20 °C
7.1: 90 percent / NEt3 / Pd(PPh3)4 / acetonitrile / 40 h / 120 °C
8.1: dicyclohexylborane / tetrahydrofuran / 2 h / 0 °C
8.2: 79 percent / NaOH; H2O / tetrahydrofuran / 1 h / 20 °C
9.1: Hg(O2CCF3)2 / tetrahydrofuran / 5 h
9.2: NaCl / H2O / 3 h / 20 °C
9.3: (n-Bu)3SnH; AIBN / toluene / 2 h / 20 - 55 °C
10.1: (PhCO2)2 / CH2Cl2 / 18 h / 80 °C
10.2: 74 percent / NH3 / methanol / 20 h / 20 °C
With
n-butyllithium; bis(cyclohexanyl)borane; ammonia; mercury(II) trifluoroacetate; sodium hydride; triethylamine; triphenylphosphine; pyridinium chlorochromate; sodium iodide; dibenzoyl peroxide;
palladium diacetate; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
1.1: Cyclization / 2.1: aminocarbonylation / 3.1: deformylation / 4.1: Oxidation / 5.1: Dehydrobromination / 5.2: Condensation / 6.1: Methylation / 7.1: Cyclization / 8.1: hydroboration / 8.2: Hydrolysis / 9.1: Addition / 9.2: Substitution / 9.3: Reduction / 10.1: Oxidation / 10.2: demethylation;
DOI:10.1002/(SICI)1521-3773(19990802)38:15<2214::AID-ANIE2214>3.0.CO;2-V