Beilstein J. Org. Chem.2013,9, 1601–1606, doi:10.3762/bjoc.9.182
Yongguang Wang Ruiyang Bao Shengdian Huang Yefeng Tang The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084, China 10.3762/bjoc.9.182 Abstract KatsumadainA, a naturally occurring influenza virus
neuraminidase (NA) inhibitor, was synthesized by using a bioinspired, organocatalytic enantioselective 1,4-conjugate addition of styryl-2-pyranone with cinnamaldehyde, followed by a tandem Horner–Wadsworth–Emmons/oxa Michael addition.
Keywords: bioinspired synthesis; catalysis; katsumadainA; natural product
; organocatalytic 1,4-conjugate addition; Introduction
2-Pyranone is a privilege structure that is often present in natural products and pharmaceuticals, many of which exhibit diverse molecular architectures and biological profiles [1][2]. For example, katsumadainA (1) and B (2), which were isolated from Alpinia
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Graphical Abstract
Scheme 1:
Proposed biosynthetic pathway and strategic analysis for synthesis of katsumadain A.