Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 12, Pages 2445-2452Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200007
Keywords
Natural products; Medicinal chemistry; Cytotoxicity; Fungal metabolites; Polyketides; Oxygen heterocycles; Configuration determination
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Funding
- National Natural Science Foundation of China (NSFC) [30925039, 81102338]
- Beijing Natural Science Foundation [5111003]
- Ministry of Science and Technology of China [2010ZX09401-403]
- Chinese Academy of Sciences [KSCX2-EW-G-6]
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Three new a-pyrones, scirpyrones AC (13), and four new pyranes, scirpyranes AD (47), were isolated from solid cultures of the plant pathogen Pestalotiopsis scirpina. Their structures were elucidated primarily by NMR experiments. The absolute configurations of C-7 and C-2' in 1, C-7 in 2, and C-6 and C-7 in 3 were deduced on the basis of circular dichroism (CD) data, whereas those of the secondary alcohols in 47 were determined by a modification of Mosher's method. Compound 1 is the first described 6-(5-oxotetrahydrofuran-2-yl)-2H-pyran-2-one. Compounds 46 showed significant cytotoxicity towards MCF-7 cells.
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