Multi-step reaction with 8 steps
1: 84 percent / Na, NH3 / 1,2-dimethoxy-ethane
2: 68 percent / DMSO, Py*SO3, Et3N
3: 65 percent / CrCl2 / tetrahydrofuran
4: 1.) Bu3SnH, AIBN, 2.) Et3N, DMAP, 3.) Pd(OAc)2, Ph3As / 1.) 80 deg C, 3.) DMF, r.t., 8 h
5: 82 percent / TBAF / tetrahydrofuran
6: 82 percent / Dess-Martin periodinane
7: 53 percent / NaN(TMS)2, HMPA / tetrahydrofuran
8: 1.) CrCl2, LiI, 2.) nBuLi, B(OMe)3, 3.) Pd(OAc)2, Ph3P, TlOH / 1.) THF, DMF, 2.) THF, -78 deg C
With
chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; n-butyllithium; TlOH; Trimethyl borate; 2,2'-azobis(isobutyronitrile); triphenyl-arsane; tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium; sulfur trioxide pyridine complex; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium iodide;
In
tetrahydrofuran; 1,2-dimethoxyethane;
DOI:10.1016/0040-4039(96)00563-1