Complestatin to chloropeptin I via a quantitative acid catalyzed rearrangement. Absolute stereochemical determination of complestatin

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Abstract

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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Jayasuriya, H., Salituro, G. M., Smith, S. K., Heck, J. V., Gould, S. J., Singh, S. B., … Patane, M. A. (1998). Complestatin to chloropeptin I via a quantitative acid catalyzed rearrangement. Absolute stereochemical determination of complestatin. Tetrahedron Letters, 39(16), 2247–2248. https://doi.org/10.1016/S0040-4039(98)00270-6

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