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. Issue 13 (1st July 2015)

• Record Type: Journal Article
• Authors: Botubol-Ares, José Manuel; Durán-Peña, María Jesús; Hernández-Galán, Rosario; Collado, Isidro G.; Harwood, Laurence M.; Macías-Sánchez, Antonio J.
• Is Part Of: Bioorganic & medicinal chemistry. Volume 23:Issue 13(2015)
• Page Start: 3379
• Page End: 3387
• Publication Date: 2015-07-01
• Subjects: Antifungal agents -- Desymmetrisation -- Lactones -- nor-Methyl mevaldate -- Statins; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2015.04.048
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: Solvent-free desymmetrisation of meso -dialdehyde1 with chiral 1-phenylethan-1-ol, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2 H -pyran-2-one (+)-3a with a 96:4 dr Deprotected lactone (+)-19a and the related racemic lactones16a –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 .