Abstract
The mechanistic and stereochemical features of a new organozinc-based substitution process [heteroatom-C-(R 1,R 2)-SPh + R 3 2Zn → heteroatom-C-(R 1,R 2,R 3)], 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.
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