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Closed Access item Intermediates with biosynthetic implications in de novo production of phenyl-phenalenone-type phytoalexins by Musa acuminata revised structure of emenolone

Authors:Gutiérrez Luis, Javier
Fletcher, Winston Q.
Echeverri, Fdo.
Abad Grillo, T.
Perales, Áurea
González-Pérez, José Antonio
Issue Date:3-Apr-1995
Publisher:Elsevier
Citation:Tetrahedron 51(14): 4117–4130 (1995)
Abstract:Three new intermediates (1 – 3) in de novo biosynthetic pathway to phenyl-phenalenone-type phytoalexins have been isolated from rhizomes of Musa acuminata infected with the fungus Fusarium oxysporum. The structures of the new pre-phytoalexins were elucidated on the basis of spectroscopic evidences, chemical correlation and acid catalyzed biomimetic cyclization of 1 to emenolone (4), isolated from the same source and whose previously reported structure has been unambiguously corrected by X-ray diffraction analysis. The chemical shift for all of the hydrogen and carbon atoms in the substances were unambiguously established by mono- and bidimensional, homo- and heteronuclear NMR experiments (1H NMR, 13C NMR, COSY, ROESY, HMQC and HMBC).
Publisher version (URL):http://dx.doi.org/10.1016/0040-4020(95)00129-V
URI:http://hdl.handle.net/10261/59872
ISSN:0040-4020
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