Absolute configuration of two new 6-alkylated a-pyrones (= 2H-pyran-2-ones) from Ravensara crassifolia

TitleAbsolute configuration of two new 6-alkylated a-pyrones (= 2H-pyran-2-ones) from Ravensara crassifolia
Publication TypeJournal Article
Year of Publication2001
AuthorsRaoelison, GE, Terreaux, C, Queiroz, EF, Zsila, F, Simonyi, M, Antus, S, Randriantsoa, A, Hostettmann, K
JournalHelvetica Chimica Acta
Volume84
Issue11
Pagination3470 - 3476
Date Published2001
Abstract

The stem bark CH2Cl2 extract of Ravensara crassifolia showed antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum in a bioautographic TLC assay. Activity-guided fractionation afforded two new a-pyrones: (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one (1) and (6R)-6[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one (2). Their structures and absolute configurations were established by NMR spectroscopy, chemical methods, and CD spectroscopy. The antifungal activity against C. cucumerinum was determined for both compounds.

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