ORGANOMETALLICS IN ORGANIC SYNTHESIS. APPLICATIONS OF A NEW DIORGANOZINC REACTION TO THE SYNTHESIS OF C-GLYCOSYL COMPOUNDS WITH EVIDENCE FOR AN OXONIUM-ION MECHANISM

Article abstract of DOI:10.1016/S0008-6215(00)90882-6

The mechanistic and stereochemical features of a new organozinc-based substitution process 1,R²)-SPh + R³₂Zn --> heteroatom-C-(R¹,R²,R³)>, first discovered during a total synthesis of the alkaloid mycotoxin α-cyclopiazonic acid, are described.Phenyl thioglycosides were valuable substrates in studying the nature of this reaction process.Since these sulfur compounds are converted into C-glycosyl compounds with some degree of stereoselectivity, the organozinc chemistry does provide a new entry to these biologically active substances.