Complestatin and isomeric chloropeptin I are bicyclo hexapeptides isolated from a Streptomyces sp. Both of these compounds are inhibitors of gp120-CD4 HIV fusion activity. In this paper, we describe an efficient acid catalyzed conversion of complestatin to chloropeptin I, provide a plausible mechanism for this transformation, and unambiguously assign the stereochemistry of complestatin.
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