Multi-step reaction with 11 steps
1: 1.) NaH, 2.) Pd(OAc)2, PPh3 / 1.) THF, 0 deg C-> r.t., 45 min, 2.) THF, 60 deg C, 30 min
2: 80 percent / TMSOTf / CH2Cl2 / 72 h / -78 - -40 °C
3: 99 percent / H2O, LiCl / dimethylformamide / 8 h / 150 °C
4: KHMDS / tetrahydrofuran / 0.5 h / -78 °C
5: 1.) mCPBA, KHCO3, 2.) NH4F / 1.) CH2Cl2, - 40 deg C -> -5 deg C, 2.) MeOH, H2O, 0 deg C, 30 min
6: 1.) Cu(OAc)2*H2O, 2.) DBU / 1.) MeOH, 0 deg C -> r.t., 2.) CH2Cl2, 0 deg C, 10 min
7: 95 percent / i-Pr2NEt / CH2Cl2 / 0.33 h / -78 °C
8: 62 percent / NaBH4, CeCl3*7H2O / methanol / 0.67 h / 0 °C
9: 83 percent / P2O5 / CHCl3 / 0.33 h / Ambient temperature
10: 1.) 9-BBN, H2O, 2.) PdCl2(dppf) K3PO4 / 1.) THF, 0 deg C -> r.t., 90 min, 2.) THF, reflux, 3 h
11: Pd(OAc)2, (R)-Tol-BINAP, K2CO3 / toluene / 1.5 h / 100 °C
With
palladium diacetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium fluoride; sodium tetrahydroborate; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; copper diacetate; (R)-2,2'-bis[bis(3-methylphenyl)phosphino]-1,1'-binaphthyl; trimethylsilyl trifluoromethanesulfonate; water; phosphorus pentoxide; potassium hexamethylsilazane; sodium hydride; potassium carbonate; potassium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium chloride;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(98)02298-9