Multi-step reaction with 7 steps
1: Et3N / tetrahydrofuran / 1 h / 0 °C
2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from 0 deg C to RT, overnight
3: 1.) TiCl4, Ti(O-iPr)4, i-Pr2NEt / 1.) CH2Cl2, 0 deg C, 90 min, 2.) CH2Cl2, 0 deg C, overnight
4: 1.) aq. LiOH, H2O2, 2.) sodium sulfite, aq. NaHCO3 / 1.) THF, 0 deg C, 3 h, 2.) THF, 2 h
5: 1.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, -78 deg C, 1 h, 2.) THF, 0 deg C, overnight
6: 300 mg / EDC, DMAP / tetrahydrofuran / Ambient temperature
7: 240 mg / aq. Na2CO3, KBr, Pd(PPh3)4 / toluene; ethanol / 6 h / 95 °C
With
titanium(IV) isopropylate; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; dihydrogen peroxide; titanium tetrachloride; sodium hydrogencarbonate; sodium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; potassium bromide; sodium sulfite;
In
tetrahydrofuran; ethanol; toluene;
DOI:10.1021/jm960465t