Multi-step reaction with 11 steps
1.1: Mg; BrCH2CH2Br / tetrahydrofuran / 10 h / Heating
1.2: 92 percent / CuBr*SMe2 / tetrahydrofuran / 4.5 h / -20 °C
2.1: 88 percent / PPh3; DEAD / tetrahydrofuran / 20 h / 0 - 20 °C
3.1: 89 percent / H2NNH2 / ethanol / 7 h / Heating
4.1: 99 percent / NEt3 / CH2Cl2 / 20 °C
5.1: 97 percent / POCl3; 2,4,6-collidine / acetonitrile / 3 h / 85 °C
6.1: LiAlH4; Me3Al / tetrahydrofuran; hexane / -78 - 20 °C
7.1: NaH / tetrahydrofuran
7.2: 85 percent / tetrahydrofuran / -78 °C
8.1: 93 percent / NEt3 / CH2Cl2 / 20 °C
9.1: 89 percent / I2; PhI(O2CCF3)2 / CH2Cl2 / -10 - 0 °C
10.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C
11.1: NaH / tetrahydrofuran / 21 h / 0 - 20 °C
11.2: 83 percent / BH3*THF / tetrahydrofuran / 0.67 h / 20 °C
With
2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; iodine; trimethylaluminum; sodium hydride; magnesium; ethylene dibromide; triethylamine; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; hydrazine; diethylazodicarboxylate; trichlorophosphate;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; acetonitrile;
1.1: Metallation / 1.2: Ring cleavage / 2.1: Mitsunobu reaction / 3.1: Hydrazinolysis / 4.1: Acetylation / 5.1: Bischler-Napieralski cyclization / 6.1: Reduction / 7.1: Metallation / 7.2: Etherification / 8.1: Tosylation / 9.1: Iodination / 10.1: Desilylation / 11.1: Diphenylphosphanylation / 11.2: Reduction;
DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W