Hemisynthesis and absolute configuration of novel 6-pentyl-2H-pyran-2-one derivatives from Trichoderma spp

• Published in: Tetrahedron Vol. 65; no. 25; pp. 4834 - 4840
• Main Authors: Daoubi, Mourad, Pinedo-Rivilla, Cristina, Rubio, M. Belen, Hermosa, Rosa, Monte, Enrique, Aleu, Josefina, Collado, Isidro G.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 20.06.2009
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Kinetics and mechanisms; Organic chemistry; Physical Sciences; Preparations and properties; Reactivity and mechanisms; Science & Technology; Trichoderma harzianum; 6-Pentyl-2H-pyran-2-one; Secondary metabolites; Detoxification mechanism; BIOTRANSFORMATION; Synthesis; Trichoderma viride; Absolute configuration; MECHANISMS; PYRONES; MODIFIED MOSHERS METHOD; METABOLITE; Stereoisomer; Metabolite; Biosynthesis; NMR spectrometry; Oxygen heterocycle; Fungi; Characterization; Ester; Gene; Reaction mechanism; Fungi Imperfecti; Transcription factor; Chemical synthesis; Secondary metabolism; Hemisynthesis; Detoxification; Lactone; Pyranone derivatives; Comparative study
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2009.04.051

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-[(1'R,2'S)-dihydroxypentyl]-2H-pyran-2-one and 6-((1'S,2'R)-2'-propyloxiran-1-yl)-2H-pyran-2-one was determined by NMR analysis of the corresponding Mosher's esters. (C) 2009 Elsevier Ltd. All rights reserved.