title: nor-Mevaldic acid surrogates as selective antifungal agent leads against Botrytis cinerea. Enantioselective preparation of 4-hydroxy-6-(1-phenylethoxy)tetrahydro-2H-pyran-2-one.
abstract: Solvent-free desymmetrisation of meso-dialdehyde 1 with chiral 1-phenylethan-1-ol, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one (+)-3a with a 96:4 dr Deprotected lactone (+)-19a and the related racemic lactones 16a-18a present a lactone moiety resembling the natural substrate of HMG-CoA reductase and their antifungal properties have been evaluated against the phytopathogenic fungi Botrytis cinerea and Colletotrichum gloeosporioides. These compounds were selectively active against B. cinerea, while inactive against C. gloeosporioides.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real, Universidad de Cádiz, Puerto Real, Cádiz 11510, Spain.
authors.forename: José Manuel
authors.initials: JM
authors.lastname: Botubol-Ares
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real, Universidad de Cádiz, Puerto Real, Cádiz 11510, Spain.
authors.forename: María Jesús
authors.initials: MJ
authors.lastname: Durán-Peña
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real, Universidad de Cádiz, Puerto Real, Cádiz 11510, Spain.
authors.forename: Rosario
authors.initials: R
authors.lastname: Hernández-Galán
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real, Universidad de Cádiz, Puerto Real, Cádiz 11510, Spain.
authors.forename: Isidro G
authors.initials: IG
authors.lastname: Collado
authors.affiliation: Department of Chemistry, University of Reading, Whiteknights, Reading RG6 6AD, United Kingdom.
authors.forename: Laurence M
authors.initials: LM
authors.lastname: Harwood
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real, Universidad de Cádiz, Puerto Real, Cádiz 11510, Spain. Electronic address: antoniojose.macias@uca.es.
authors.forename: Antonio J
authors.initials: AJ
authors.lastname: Macías-Sánchez
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D020171:Botrytis / Q000187:drug effects* / Q000254:growth & development / Q000302:isolation & purification; D020231:Colletotrichum / Q000187:drug effects* / Q000254:growth & development / Q000302:isolation & purification; D015169:Colony Count, Microbial; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology; D005976:Glutaral / Q000031:analogs & derivatives* / Q000737:chemistry; D025782:Hydroxymethylglutaryl-CoA-Reductases, NADP-dependent / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D018716:Molecular Mimicry; D010626:Phenylethyl Alcohol / Q000737:chemistry; D010935:Plant Diseases / Q000382:microbiology; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D027843:Vitis / Q000382:microbiology
chemical_list: D000447:Aldehydes; D005659:Fungicides, Industrial; D007783:Lactones; D011714:Pyrans; D025782:Hydroxymethylglutaryl-CoA-Reductases, NADP-dependent; D010626:Phenylethyl Alcohol; D005976:Glutaral; C005261:mevaldic acid
keywords: Antifungal agents; Desymmetrisation; Lactones; Statins; nor-Methyl mevaldate