Multi-step reaction with 12 steps
1.1: 3.50 g / lead(IV) acetate / CH2Cl2 / 20 °C
2.1: 53 percent / (-)-N-(1-phenylethyl)-1-azabicyclo[2.2.2]octan-3-amine; lithium chloride; n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C
3.1: m-chloroperoxybenzoic acid / CH2Cl2 / 4 h / 20 °C
4.1: florisil / CH2Cl2 / 2 h
5.1: 4.90 g / IBX / dimethylsulfoxide / 1 h / 20 °C
6.1: 4.36 g / N,N-dimethylaniline / CH2Cl2 / -78 - 20 °C
7.1: 73 percent / tributyltin hydride; BEt3; air / toluene; hexane / 0.5 h / 20 °C
8.1: N,N-diisopropylethylamine / CH2Cl2 / 4 h / -20 °C
9.1: CH2Cl2 / 3 h / 35 °C
9.2: 356 mg / 3-chloroperoxybenzoic acid / CH2Cl2 / 1 h / 20 °C
10.1: 78 percent / 3-chloroperoxybenzoic acid; BF3*OEt2 / CH2Cl2 / 0.17 h / 20 °C
11.1: 73 percent / L-selectride / tetrahydrofuran / 0.25 h / -78 °C
12.1: 92 percent / tributylamine; triphenylphosphine; formic acid / palladium(II) acetate / dimethylformamide / 2 h / 40 °C
With
lead(IV) acetate; florisil; n-butyllithium; formic acid; air; tributyl-amine; triethyl borane; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; L-Selectride; N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
palladium diacetate;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0700474