Multi-step reaction with 7 steps
1: 1.) N,N-diisopropylethylamine, n-BuLi / 1) THF, -78 deg C, 20 min; 2) THF, -78 deg C, 1 h
2: 1.) pTSA, 2.) Et3N / 1) CH3OH, H2O, reflux, 11 h; 2) CH3OH, H2O, rt, 30 min
3: 89 percent / NaI, Bu3SnH, AIBN / 1,2-dimethoxy-ethane / 5 h / Heating
4: 82 percent / Et3N, DMAP / CH2Cl2 / 12 h / Ambient temperature
5: 62 percent / NH3, AlMe3 / CH2Cl2; toluene / 2 h / Ambient temperature
6: 61 percent / K2CO3 / CHCl3 / 9 h / Heating
7: 1.) HCl, 2.) Me3Al / 1) EtOAc, 0 deg C, 15 min; 2) CH2Cl2, toluene, 25 min; 3) CH2Cl2, toluene, 35 deg C, 9.5 h
With
hydrogenchloride; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); ammonia; trimethylaluminum; tri-n-butyl-tin hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide;
In
1,2-dimethoxyethane; dichloromethane; chloroform; toluene;
DOI:10.1021/jo960315q