Structure assignment, total synthesis, and antiviral evaluation of cycloviracin B1

…, J Mlynarski, M Matheu, E DeClercq

Index: Fuerstner, Alois; Albert, Martin; Mlynarski, Jacek; Matheu, Maribel; DeClercq, Erik Journal of the American Chemical Society, 2003 , vol. 125, # 43 p. 13132 - 13142

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Citation Number: 75

Abstract

The first total synthesis of the antivirally active glycolipid cycloviracin B1 (1) is described. The approach is based on a two-directional synthesis strategy which constructs the C 2- symmetrical macrodiolide core of the target by an efficient template-directed macrodilactonization reaction promoted by 2-chloro-1, 3-dimethylimidazolinium chloride 14 as the activating agent. Attachment of the lateral fatty acid chains to the lactide core thus ...