Multi-step reaction with 6 steps
1: 1.) chlorotrimethylsilane, Et3N, 2.) Et3N, Pb(NO3)2 / 1) CH2Cl2, reflux, 1 h; 2) CH2Cl2, MeOH, rt, 96 h
2: 100 percent / DMSO, oxalyl chloride / CH2Cl2 / 0.5 h / -60 °C
3: 1.) NaHMDS, 2.) MoOPH / 1) THF, -78 deg C, 2 h; 2) THF, -78 - -15 deg C, 2.5 h
4: 92 percent / NaBH4 / methanol; tetrahydrofuran / 4 h / -78 °C
5: 97 percent / PPTS / dimethylformamide; acetone / 24 h / 5 °C
6: 1.) n-BuLi, 2.) LiClO4 / 1) hexane, THF, -78 - -65 deg C, 5 min; 2) THF, hexane, -78 deg C, 2 h
With
sodium tetrahydroborate; n-butyllithium; chloro-trimethyl-silane; lead(II) nitrate; oxalyl dichloride; MoO5*pyridine*HMPA; lithium perchlorate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo9604245