880152-89-6Relevant academic research and scientific papers
Pentenolide analogues of antifungal butenolides: Strategies towards 3,6-disubstituted pyranones and unexpected loss of biological effect
Snajdr, Ivan,Pavlik, Jan,Schiller, Radan,Kunes, Jiri,Pour, Milan
, p. 1472 - 1498 (2008/09/17)
Pentenolide analogues of antifungal 3,5-disubstituted butenolides were prepared by oxidative cyclization of 2-(substituted aryl)hex-5-enoic acids as the key step. Given the limitations of the methodology, another approach to the title compounds based on the Pd-catalyzed carbonylative lactonization of 4-iodo-3-en-1-ols was developed, and the carbonylation conditions were optimized. While the former sequence allows only the introduction of a substituted methyl at C6, pyranones bearing a range of various C-substituents at C6 can be prepared by the latter. Somewhat surprisingly, unlike the corresponding butenolides with the same substitution pattern, the title pentenolides possess no antifungal or cytostatic activity.
