156947-99-8Relevant articles and documents
VINYL ETHER HYDROLYSIS. 30. EFFECT OF β-CARBOXY AND β-CARBOMETHOXY SUBSTITUTION
Kresge, A. J.,Ubysz, D.
, p. 316 - 322 (1994)
Rates of hydrolysis of the vinyl ether functional groups of (Z)- and (E)-β-methoxyacrylic acid and (Z)- and (E)-β-methoxymethacrylic acid and their methyl esters were measured in aqueous perchloric acid solution.Additional rate measurements were also made for one substrate, (Z)-β-methoxymethacrylic acid, in buffer solutions down to pH 7, and a rate profile was constructed.The results show that the β-carboxy and β-carbomethoxy substituents produce strong rate retardations, ranging from 2000- to 25 000-fold, for both Z- and E-isomers in both the acrylic and methacrylic acid series.The rate profile for (Z)-β-methoxymethacrylic acid indicates that ionization of this substrate to the carboxylate ion form raises the rate of hydrolysis by a factor of 240.It is argued that this difference in reactivity of ionized and non-ionized forms of the substrate is due to conjugative and inductive effects of the substituents, rather than β-lactone formation as suggested in an earlier observation of the same phenomenon in a different system.
Synthesis of the eastern portion of ajudazol a based on stille coupling and double acetylene carbocupration
Krebs, Oliver,Taylor, Richard J. K.
, p. 1063 - 1066 (2005)
(Chemical Equation Presented) A strategy for the synthesis of ajudazol A, an unusual, pharmacologically active metabolite from myxobacteria, based on the Stille cross-coupling of a 2-stannyl-oxazole with a vinyl iodide unit is described; the vinyl halide unit containing a (Z,Z)-diene was prepared in one pot by the double acetylene carbocupration of a functionalized alkyl cuprate followed by trapping with 2,3-dibromopropene.
Isobenzofurans as Synthetic Intermediates: Synthesis and Biological Activity of 8-epi-(–)-Ajudazol B
Adair, Liam,Egan, Ben A.,Pearson, Colin M.,Lopez-Gonzalez, Ricardo,Kuchar, Michal,Mendoza-Mendoza, Artemio,Prunet, Jo?lle,Marquez, Rodolfo
supporting information, p. 6661 - 6672 (2020/10/15)
Ajudazol B is a polyketide secondary metabolite, isolated from the myxobacterium Chondromyces crocatus, that exhibits potent biological activity. Herein, we report a convergent total synthesis of 8-epi-(–)-ajudazol B. The key step is a regio-selective alk
Total Synthesis of Ajudazol A by a Modular Oxazole Diversification Strategy
Essig, Sebastian,G?lz, Jan Philipp,Menche, Dirk,Von Schwarzenberg, Karin,Wollnitzke, Philipp
supporting information, (2020/09/02)
The total synthesis of the potent respiratory chain inhibitor ajudazol A was accomplished by a concise strategy in 17 steps (longest linear sequence). The modular approach was based on a direct oxazole functionalization strategy involving a halogen dance
PANTETHEINE DERIVATIVES AND USES THEREOF
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Paragraph 2121, (2020/06/19)
The present disclosure relates to compounds of Formula (I), (II), or (II'): (I), (II), (II'), and pharmaceutically acceptable salts or solvates thereof. The present disclosure also relates to pharmaceutical compositions comprising the compounds and therapeutic and diagnostic uses of the compounds and pharmaceutical compositions.
Full stereochemical determination of ajudazols a and b by bioinformatics gene cluster analysis and total synthesis of ajudazol B by an asymmetric ortholithiation strategy
Essig, Sebastian,Bretzke, Sebastian,Müller, Rolf,Menche, Dirk
supporting information, p. 19362 - 19365 (2013/02/21)
The stereochemical determination of the potent respiratory chain inhibitors ajudazols A and B and the total synthesis of ajudazol B are reported. Configurational assignment was exclusively based on biosynthetic gene cluster analysis of both ketoreductase
Iridium-catalyzed asymmetric hydrogenation of vinyl ethers
Zhu, Ye,Burgess, Kevin
supporting information; experimental part, p. 979 - 983 (2009/05/30)
A carbene-oxazoline catalyst 1 proved to be an effective catalyst for reduction of an enol ether that the literature suggested could not be hydrogenated effectively by P,N-Ir catalysts. Thus, a series of ester and alcohol substrates were hydrogenated using catalyst 1. Good to excellent enantioselectivities and high conversions were obtained.
Haloacetylated Enol Ethers. 8 [12]. Reaction of β-Alkoxyvinyl Trihalomethyl Ketones with Guanidine Hydrochloride. Synthesis of 4-Trihalomethyl-2-Aminopyrimidines
Zanatta, Nilo,Cortelini, Maria De F. M.,Carpes, Marcos J. S.,Bonacorso, Helio G.,Martins, Marcos A. P.
, p. 509 - 513 (2007/10/03)
In this work the results of the reaction of β-alkoxyvinyl trihalomethyl ketones 1, 2a-e, with guanidine hydrochloride are reported. Depending on the ketone 1 or 2 and the conditions under which the reactions were carried out, 4-trihalomethyl-2-amino pyrimidines, β-alkoxyvinyl carboxylic acids, or β-acetal carboxylic esters were obtained.
