Hemisynthesis and Absolute Configuration of novel 6-pentyl-2H-pyran- 2-one derivatives from Trichoderma spp

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URI: http://hdl.handle.net/10498/17357
DOI: 10.1016/j.tet.2009.04.051
ISSN: 0040-4020
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2009-04-18Department
Química OrgánicaSource
Tetrahedron, 2009 Vol.65, pp. 4834–4840Abstract
A comparative study of the secondary metabolism of two Trichoderma spp. with that of the Thctf1
transcription factor gene null mutant of Trichoderma harzianum 34 was carried out in order to deepen our
knowledge of the biosynthetic pathway and mode of action of 6-pentyl-2H-pyran-2-one (1) and its
derivatives as biocontrol agents. New isolated metabolites have shed light on the detoxification
mechanism of 6-pentyl-pyranone by Trichoderma spp. All new compounds were synthesized and their
stereoisomer characterized. The absolute configuration of 6-[(10R,20S)-dihydroxypentyl]-2H-pyran-2-one
and 6-((10S,20R)-20-propyloxiran-1-yl)-2H-pyran-2-one was determined by NMR analysis of the corresponding
Mosher’s esters.
Subjects
trichoderma; pyrone; 6-Pentyl-2H-pyran-2-one; trichoderma viride; trichoderma harzianum; secondary metabolites; synthesis; Absolute configuration; Detoxification mechanismCollections
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