Multi-step reaction with 17 steps
1: 6.5 g / diethyl ether / 0.5 h / -65 - 20 °C
2: 85 percent / (i-Pr)2NEt
3: TiCl4; TMEDA; Zn / PbCl2 / CH2Cl2
4: PhCH=RuCH{[(Mes)NCH2CH2N(Mes)]}(PCy3)Cl2 / benzene / 20 °C
5: 92 percent / m-CPBA
6: 78 percent / NaH / tetrahydrofuran
7: PPTS; pyridine / toluene / 100 °C
8: 97 percent / DDQ; H2O / CH2Cl2
9: DEAD; PPh3 / toluene
10: NaOH / tetrahydrofuran; methanol
11: 97 percent / NEt3 / dimethylformamide
12: 97 percent / NaBH4 / ethanol / 2 h / -65 - 20 °C
13: 95 percent / TsOH*H2O / various solvent(s) / 0.5 h / 0 °C
14: 98 percent / NEt3; TMSOTf / CH2Cl2 / 1 h / -60 - 0 °C
15: 95 percent / PhCH=Ru{[(Mes)NCH2CH2N(Mes)]}(PCy3)Cl2 / benzene / 8 h / 20 °C
16: dimethyldioxirane / CH2Cl2; acetone / 0.5 h / -60 - 20 °C
17: 2.0 mg / i-Bu2AlH / CH2Cl2; hexane / 0.3 h / -60 - 20 °C
With
pyridine; sodium hydroxide; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate; water; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; diethylazodicarboxylate;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(II) chloride;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
9: Mitsunobu inversion;
DOI:10.1002/chem.200500993