1. 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.
- Author
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Botubol-Ares JM, Durán-Peña MJ, Hernández-Galán R, Collado IG, Harwood LM, and Macías-Sánchez AJ
- Subjects
- Aldehydes chemistry, Botrytis growth & development, Botrytis isolation & purification, Colletotrichum growth & development, Colletotrichum isolation & purification, Colony Count, Microbial, Fungicides, Industrial pharmacology, Glutaral chemistry, Hydroxymethylglutaryl-CoA-Reductases, NADP-dependent chemistry, Lactones chemistry, Molecular Mimicry, Phenylethyl Alcohol chemistry, Plant Diseases microbiology, Pyrans pharmacology, Stereoisomerism, Structure-Activity Relationship, Vitis microbiology, Botrytis drug effects, Colletotrichum drug effects, Fungicides, Industrial chemical synthesis, Glutaral analogs & derivatives, Pyrans chemical synthesis
- 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., (Copyright © 2015 Elsevier Ltd. All rights reserved.)
- Published
- 2015
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