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Zav’yalov, S. I.; Дорофеева, О. В.; Rumyantseva, E. E.; Kulikova, L. B.; Ezhova, G. I.; Kravchenko, N. E.; Zavozin, A. G.

doi:10.1023/a:1010477022450

Cited by 13 publications

(5 citation statements)

References 10 publications

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“…We next aimed to develop a general strategy for the introduction of the imidazolone substructure present in the targeted pre-agelastatin 16 39. Initially, we focused on the direct addition of transmetallated derivatives of triazone 27 (Scheme 2, metal = Li, Mg, Cu, Ce, Zn) to the bicyclic C5-ester (+)- 21 .…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of all (−)-agelastatin alkaloids

2010

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The pyrrole-imidazole family of marine alkaloids, derived from linear clathrodin-like precursors, constitutes a diverse array of structurally complex natural products. The bioactive agelastatins are members of this family that possess a tetracyclic molecular framework incorporating C4–C8 and C7–N12 bond connectivities. We provide a hypothesis for the formation of the unique agelastatin architecture that maximally exploits the intrinsic chemistry of plausible biosynthetic precursors. We report the concise enantioselective total syntheses of all known agelastatin alkaloids including the first total syntheses of agelastatins C, D, E, and F. Our gram-scale chemical synthesis of agelastatin A was inspired by our hypothesis for the biogenesis of the cyclopentane C-ring and required the development of new transformations including an imidazolone-forming annulation reaction and a carbohydroxylative trapping of imidazolones.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of all (−)-agelastatin alkaloids

2010

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“…It is well known that the thiazole derivatives are important compounds due to their broad range of biological activities [1][2][3]. 2-Aminothiazoles as well as 2-amino-4-arylthiazoles and their derivatives have shown radioprotective [4,5], bactericidal, antifungal [6][7][8], antiviral [9,10], insecticidal [8], and anesthetic [11][12][13] activities.…”

Section: Introductionmentioning

confidence: 99%

Preparation, antimicrobial activity, and toxicity of 2‐amino‐4‐arylthiazole derivatives

Morales-Bonilla

Perez‐Cardena

Quintero-Mármol

et al. 2006

Heteroatom Chemistry

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“…vi,x To our delight, the triazone moiety in 28 could be readily hydrolyzed in the presence of aqueous hydrochloric acid in methanol at 23 °C. The 2,3-disubstituted imidazolone 30 was obtained in 83% yield through a condensative cyclization of a putative keto-urea intermediate 29 (Scheme 2).…”

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confidence: 99%