Either the C2‐ or the C3‐substituted product can be obtained with the same palladium(II) catalyst in an oxidative intermolecular alkenylation of indoles. A variety of conditions can be used for derivatization at the 3‐position; however, the presence of acetic acid is required for the C2‐selective process (see scheme). Further elaboration of the products by a similar CH functionalization process leads to the bisalkenylated indoles selectively.
The strobilurins and oudemansins are natural β‐methoxyacrylates which inhibit mitochondrial respiration and, as a result, have fungicidal activity. A knowledge of the structures (configuration and conformation) and properties of these compounds has allowed the preparation of analogues in which both fungicidal activity and stability have been improved.
Das C2‐ oder das C3‐substituierte Produkt kann bei der oxidativen intermolekularen Alkenylierung von Indolen mit dem gleichen Palladium(II)‐Katalysator erhalten werden. Eine Vielzahl an Bedingungen eignet sich für die Derivatisierung an der 3‐Position; dagegen erfordert der C2‐selektive Prozess Essigsäure (siehe Schema). Eine weitere ähnliche C‐H‐Funktionalisierung überführt die Produkte selektiv in die bisalkenylierten Indole.
In the presence of suitable rhodium(ii) catalysts, lactam derived P-ketosulfoxonium ylides can be transformed to P-oxonitrogen heterocycles, e.g. substituted 4-oxopyrrolidine, via intermediates of carbenoid nature.In the course of our study into new routes to non-proteinogenic amino acids it proved necessary to develop a procedure that would convert a chiral azetidin-2-one (e.g. 1) to a substituted 4-oxopyrrolidine 2 (Scheme 1). Previously, we reported that a suitably activated P-lactam 3 can be efficiently ring opened with dimethylsulfoxonium methylide to produce the P-ketosulfoxonium ylide 4, which could then be converted to a series of &substituted y-oxo-a-aminoacids 5 (Scheme 2).1 1 2 Scheme 1 3 4 5
Extensive molecular modeling based on crystallographic data was used to aid the design of synthetic analogues of the fungicidal naturally occurring respiration inhibitors crocacins A and D, and an inhibitor binding model to the mammalian cytochrome bc 1 complex was constructed. Simplified analogues were made which showed high activity in a mitochondrial beef heart respiration assay, and which were also active against certain plant pathogens in glasshouse tests. A crystal structure was obtained of an analogue of crocacin D bound to the chicken heart cytochrome bc 1 complex, which validated the binding model and which confirmed that the crocacins are a new class of inhibitor of the cytochrome bc 1 complex.
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