Solid-support based total synthesis and stereochemical correction of brunsvicamide A.
Solid-support based total synthesis and stereochemical correction of brunsvicamide A.
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DOI：
10.1021/ol801064d
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发表时间：
2008-07
期刊：
影响因子：
5.2
通讯作者：
T. Walther;Hans‐Dieter Arndt;H. Waldmann
中科院分区：
文献类型：
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作者：
T. Walther;Hans‐Dieter Arndt;H. Waldmann
报道了蓝藻代谢产物brunsvicamide A的全合成及其原来指定的立体化学的校正。关键要素是尿素结构单元的构建、肽在固相上的延伸和肽链在树脂上的环化，具有良好的总产率。详细的结构研究发现，brunsvicamide A在其骨架中具有以前未检测到的d-赖氨酸残基，为该类化合物的所有进一步研究奠定了基础。
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.