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Synthesis of a natural product-inspired eight-membered ring lactam library via ring-closing metathesis
Authors:Brown Neil  Xie Baohan  Markina Nataliya  Vandervelde David  Perchellet Jean-Pierre H  Perchellet Elisabeth M  Crow Kyle R  Buszek Keith R
Institution:aDepartment of Chemistry, University of Missouri-Kansas City, 205 Spencer Chemical Laboratories, 5100 Rockhill Road, Kansas City, MO 64110, USA;bCenter for Chemical Methodologies and Library Development, University of Kansas, 1501 Wakarusa Drive, Lawrence, KS 66047, USA;cAnti-Cancer Drug Laboratory, Kansas State University, Division of Biology, Ackert Hall, Manhattan, KS 66506, USA
Abstract:We have prepared a novel speculative eight-membered lactam demonstration library based on the skeletal structure of the potent antitumor marine natural product octalactin A. The basic scaffold was readily constructed in a convergent fashion via ring-closing metathesis chemistry from the corresponding diene amides. A cursory examination of the biological properties of the library validates the relevance and significance of these structures.
Keywords:Eight-membered  Natural product  Lactam  Library  Ring-closing metathesis  Medium-ring  Octalactin  Parallel synthesis
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