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

Raoelison, Guy Emmanuel
Terreaux, Christian
Queiroz, Emerson Ferreira
Zsila, F.
Simonyi, M.
Antus, S.
Randriantsoa, A.
Published in Helvetica Chimica Acta. 2001, vol. 84, p. 3470-3476
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 alpha -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.
Keywords 1,3-diol acetonideslactonesRavensara crassifoliaNMR spectroscopy
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