Multi-step reaction with 12 steps
1: 94 percent / N,N-diisopropylethylamine, tetrabutylammonium iodide / CH2Cl2 / 18 h / Ambient temperature
2: 1.) BuLi, 4 Angstroem molecular sieves, 2.) LiBr / 1) THF, hexane, -50 to -40 deg C, 1 h; 2) THF, hexane, -40 deg C, 15 min; 3) THF, hexane, -50 to -40 deg C, 1 h, -40 deg C, 1.5 h
3: H2 / Pd/CaCO3 / 24 h
4: 95 percent / N,N-diisopropylethylamine, tetrabutylammonium iodide / CH2Cl2 / 19 h / Ambient temperature
5: 99 percent / HF*pyridine / pyridine; tetrahydrofuran / 3.5 h
6: 99 percent / Dess-Martin periodinane / CH2Cl2 / 0.58 h
7: tetrahydrofuran; hexane / 1) -78 deg C, 5 min; 2) rt, 2.5 h
8: 1.) t-BuLi, 2.) 9-methoxy-9-borabicyclo<3.3.1>nonane, 3.) PdCl2(dppf), aq. K3PO4 / 1) Et2O, pentane, -78 deg C, 3 min; 2) Et2O, pentane, hexane, THF, -78 deg C, 10 min, -78 deg C --> rt, 1.25 h; 3) Et2O, pentane, THF, hexane, FMF, rt, 16 h
9: 79 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 18 h / -50 °C
10: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h
11: 98 percent / aq. NaClO2, NaH2PO4*H2O, 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / Ambient temperature
12: 82 percent / benzene; methanol / 0.25 h
With
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium chlorite; potassium phosphate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 4 A molecular sieve; hydrogen; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; 9-methoxy-9-BBN; lithium bromide;
Lindlar's catalyst;
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; tert-butyl alcohol; benzene;
DOI:10.1021/jo9811423