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Asymmetric Synthesis of (-)-Catunaregin, an Angiogenesis Inhibitor from Mangroves
Arun K Ghosh1, Christopher Vultorius1
1Department of Chemistry, Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907, United States.
Abstract:
We describe here an enantioselective synthesis of (-)-catunaregin (1), a bioactive agent from Mangrove plants. Our synthesis features an Evans' asymmetric syn-aldol reaction, cross-metathesis to an enone, substrate controlled 1,4-addition, a one-pot cyclization to construct the O-bridged tetrahydrofuropyran core, and deprotection to furnish (-)-catunaregin (1). Our synthetic investigations into the synthesis of (-)-epicatunaregin (2) from a common intermediate resulted in an interesting structural variant, which was fully characterized by X-ray diffraction analysis. The present synthesis provides convenient access to enantiomeric catunaregin natural products and their structural variants.
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