ChemInform Abstract: Mechanism, Biological Relevance, and Structural Requirements for Thiolate Additions to Bicyclomycin and Analogues: A Unique Latent Michael Acceptor System.

Abstract

352ChemInform Abstract The derivatives (Ia)-(If) of the antibiotic bicyclomycin (Ig) are synthesized and examined for thiolate addition to the C-5 exo-methylene group by method A). A diastereomeric mixture of the sulfide adducts (IIa) is obtained from (Ia), whereas (Ib) yields only minor amounts of (IIb). In contrast, (Ie) is converted to the optically active product (IV). (Ic), (Id) and (If) are recovered unchanged. The results are discussed in the context of a recently proposed mechanism of action for bicyclomycin.