Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics.In a document type is Article, the author is Fuerstner, Alois and a compound is mentioned, 69778-83-2, 4-Methoxy-1H-pyrrol-2(5H)-one, introducing its new discovery. 69778-83-2
Total synthesis, molecular editing and evaluation of a tripyrrolic natural product: The case of “butylcycloheptylprodigiosin”
Conflicting reports are found in the literature on whether the ortho-pyrrolophane derivative 6, which has been named ” butylcycloheptylprodigiosin” even though it is a cyclononane derivative, is a natural product or merely a mis-assigned structure. This dispute has now been resolved by an unambiguous total synthesis of this complex alkaloid which confirms the initial structure assignment. The chosen approach is largely catalysis-based, featuring the first application of a “Narasaka-Heck” reaction in natural product chemistry. This palladium-catalyzed transformation allows the unsaturated oxime ester 26 to be converted into the bicyclic dihydropyrrole 27. Other notable reactions of the reported approach to 6 are a regioselective Tsuji-Trost reaction of the doubly allylic acetate 21 with methyl acetoacetate. a base-induced aromatization of 27 to the corresponding pyrrole 28. a chemoselective oxidation of the benzylic methyl group in 33 with cerium ammonium nitrate in a biphasic reaction medium that does not affect the labile pyrrole nucleus, and a Suzuki cross-coupling for the completion of the heterocyclic domain. Diversification in the latter step leads to a set of analogues that differ from the natural product in the terminal (hetero)arene ring. This structural modification results in complete loss of the very pronounced ability of the parent compound 6 to induce oxidative cleavage in double stranded DNA in the presence of Cu11. Several cyclononane-, cyclononene- and cyclononadiene derivatives prepared en route to 6 have been characterized by crystal structure analysis, allowing the conformational behavior of nine-membered carbocycles to be studied.
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Reference£º
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem