Lazzara, Nicholas C.; Rosano, Robert J.; Vagadia, Purav P.; Giovine, Matthew T.; Bezpalko, Mark W.; Piro, Nicholas A.; Kassel, Wm. Scott; Boyko, Walter J.; Zubris, Deanna L.; Schrader, Kevin K.; Wedge, David E.; Duke, Stephen O.; Giuliano, Robert M. published the artcile< Synthesis and Biological Evaluation of 6-[(1R)-1-Hydroxyethyl]-2,4a(R),6(S),8a(R)-tetrahydropyrano-[3,2-b]-pyran-2-one and Structural Analogues of the Putative Structure of Diplopyrone>, Reference of 4098-06-0, the main research area is hydroxyethyl tetrahydropyrano pyranone analog preparation fungicide antibiotic phytotoxic catfish.
The phytotoxin diplopyrone is considered to be the main phytotoxin in a fungus that is responsible for cork oak decline. A carbohydrate-based synthesis of the enantiomer of the structure proposed for diplopyrone has been developed from a com. available derivative of D-galactose. Key steps in the synthesis are a highly stereoselective pyranose chain-extension based on methyltitanium, preparation of a vinyl glycoside via Isobe C-alkynylation-rearrangement/reduction, and RCM-based pyranopyran construction. Crystallog. and NMR anal. confirms an earlier report that the structure originally proposed for diplopyrone may require revision. Structural analogs were prepared for biol. evaluation, the most promising being a pyranopyran nitrile synthesized from tri-O-acetyl-D-galactal by Ferrier cyanoglycosidation, Wittig chain extension, and lactonization. Biol. assays revealed potent antibacterial activity for the nitrile analog against common bacterial pathogens Edwardsiella ictaluri and Flavobacterium columnare that cause enteric septicemia (ESC) and columnaris disease, resp., in catfish. The IC50 value of 0.002 against E. ictaluri indicates approx. 100 times greater potency than the antibiotic florfenicol used com. for this disease. Phytotoxic activity for all three target compounds against duckweed was also observed The antibiotic and phytotoxic activities of the new pyranopyrans synthesized in this study demonstrate the potential of such compounds as antibiotics and herbicides.
Journal of Organic Chemistry published new progress about Alkynylation. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Reference of 4098-06-0.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics