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A total synthesis of the cyanobacterial metabolite brunsvicamide A and the correction of its originally assigned stereochemistry are reported. Key elements were the construction of a urea building block, peptide elongation on solid phase, and on-resin cyclization of the peptide chain, with good overall yield. Detailed structural investigations uncovered that brunsvicamide A features a previously undetected d-lysine residue in its backbone, setting the foundation for all further investigations in this compound class.

Citation

Thilo Walther, Hans-Dieter Arndt, Herbert Waldmann. Solid-support based total synthesis and stereochemical correction of brunsvicamide A. Organic letters. 2008 Aug 7;10(15):3199-202

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PMID: 18590275

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