Multi-step reaction with 16 steps
1.1: n-BuLi / diethyl ether / -78 °C
1.2: MgBr2*OEt2 / diethyl ether / -78 - 0 °C
1.3: THF / diethyl ether / 20 °C
2.1: 4-dimethylaminopyridine; pyridine / CH2Cl2
3.1: (S)-1-Me-3,3-diPh-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole; BH3*SMe2 / tetrahydrofuran / 0 °C
4.1: H2; pyridine / Pd/CaCO3/Pb / benzene / 760.05 Torr
4.2: 4-dimethylaminopyridine; imidazole / dimethylformamide
5.1: K2CO3 / methanol
6.1: SO3*pyridine; dimethylsulfoxide; iPr2NEt / CH2Cl2 / -25 °C
7.1: 74 percent / HF*pyridine; pyridine / tetrahydrofuran / 0 °C
8.1: 92 percent / pyridinium p-toluenesulfonate; HC(OMe)3 / CH2Cl2 / -10 °C
9.1: 88 percent / H2O2; [(NH4)6Mo7O24] / methanol / 0 °C
10.1: 92 percent / LiAlH4 / diethyl ether / -20 °C
11.1: 98 percent / imidazole / dimethylformamide
12.1: lithium diisopropylamide / tetrahydrofuran / -78 °C
13.1: Dess-Martin periodinane; pyridine / CH2Cl2
14.1: 92 percent / Na/Hg; NaH2PO4 / tetrahydrofuran; methanol / -10 °C
15.1: tetrabutylammonium fluoride / tetrahydrofuran / -20 °C
16.1: pyridinium p-toluenesulfonate / CH2Cl2 / 0 °C
With
pyridine; 1H-imidazole; dmap; sodium dihydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; pyridine-SO3 complex; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; trimethyl orthoformate;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
3.1: Corey-Bakshi-Shibata reduction / 6.1: Parikh-Doering oxidation / 13.1: Dess-Martin oxidation;
DOI:10.1002/anie.200701515