期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 350, 期 1, 页码 65-69出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700283
关键词
electron transfer; ketyl-aryl coupling; polycycles; radical reactions; samarium diiodide; steroids
Treatment of naphthyl-substituted cyclopentane-1,3-diones with the samarium diiodidehexamethylphosphoramide (HMPA) complex in the presence of tert-butyl alcohol provided the expected tetracyclic diols with steroid-like structures. Surprisingly, reactions without the proton source led to the efficient formation of a new pentacyclic diol. In this case the toxic additive HMPA could be substituted by a combination of lithium bromide (in situ generation of samarium dibromide) and N,N-dimethylimidazolidone. The styrene-like alkene moiety of this product was used to prepare an ensemble of highly substituted pentacyclic steroid-like compounds.
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