Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection

Sellstedt, Magnus; Schwalfenberg, Melanie; Ziegler, Slava; Antonchick, Andrey P.; Waldmann, Herbert

doi:10.1039/c5ob02272j

Cited by 11 publications

(7 citation statements)

References 39 publications

(31 reference statements)

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“…Henceforth, an impressive, flourishing number of reports appeared by these and other research groups, which focused on the ε,β-regioselective [4 + 2] cycloaddition between polyenals and a wide array of diverse dienophiles ranging from nitroalkenes, alkylidene heterocycles, to azadienes, enones, etc. For an immediate glance at this varied reaction panorama, a table is given (Table ), collectively depicting these contributions. − …”

Section: Vinylogous Aldehydesmentioning

confidence: 99%

New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems

et al. 2020

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The principle of vinylogy states that the electronic effects of a functional group in a molecule are possibly transmitted to a distal position through interposed conjugated multiple bonds. As an emblematic case, the nucleophilic character of a π-extended enolate-type chain system may be relayed from the legitimate α-site to the vinylogous γ, ε, ..., ω remote carbon sites along the chain, provided that suitable HOMO-raising strategies are adopted to transform the unsaturated pronucleophilic precursors into the reactive polyenolate species. On the other hand, when “unnatural” carbonyl ipso -sites are activated as nucleophiles (umpolung), vinylogation extends the nucleophilic character to “unnatural” β, δ, ... remote sites. Merging the principle of vinylogy with activation modalities and concepts such as iminium ion/enamine organocatalysis, NHC-organocatalysis, cooperative organo/metal catalysis, bifunctional organocatalysis, dicyanoalkylidene activation, and organocascade reactions represents an impressive step forward for all vinylogous transformations. This review article celebrates this evolutionary progress, by collecting, comparing, and critically describing the achievements made over the nine year period 2010–2018, in the generation of vinylogous enolate-type donor substrates and their use in chemical synthesis.

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Section: Vinylogous Aldehydesmentioning

confidence: 99%

New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems

et al. 2020

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“…In this study, alkyl‐substituted 2,4‐dienals 8 , in situ generates active trienamine species by using aminocatalyst Cat.11 , which undergo a cycloaddition reaction with maleimide derivatives 50 followed by a Wittig reaction to avoid the isolation of unstable products, leading to the formation of hexahydroisoindole unsaturated ester compounds 51 in fair to good yields and good to excellent stereoselectivities. The study also demonstrated that hexahydroisoindole moiety is present in naturally occurring Cytochalasin B (Scheme ) …”

Section: Dienals and Dienones In Trienamine Catalysismentioning

confidence: 83%

Polyenals and Polyenones in Aminocatalysis: A Decade Building Complex Frameworks from Simple Blocks

et al. 2020

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Polyenals and polyenones are simple chemical compounds which can be constructed into large and complex structures by virtue of aminocatalysis. In the past eight years, new aminocatalytic activation modes based on trienamine, cross-trienamine, tetraenamine, iminium ion, and vinylogous iminium ion intermediates have attracted great attention in the field of asymmetric synthesis. Key to the increasing focus is their inherent ability to allow functionalization of remote sites with excel-[a] Dr.

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“…23 Although over 400 cytochalasans were isolated from natural sources 24 and the X-ray crystal structure of a complex of CytD (2) with actin is known, 25 limited knowledge exists regarding their structure-activity relationship (SAR). [26][27][28][29] In general, there are two important factors that contribute to the biological activity: 1) an intact macrocyclic ring that contains several stereogenic centres and double bonds; 30 and 2) C-7 hydroxy group [30][31][32] (such as in CytB, 1, and CytD, 2) or an epoxy group C-6 and C-7 (ref. 32) (such as in cytochalasin E, 3).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and migrastatic activity of cytochalasin analogues lacking a macrocyclic moiety

Formánek,

Dupommier,

Volfová

et al. 2024

RSC Med. Chem.

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Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection

Abstract: Asymmetric trienamine catalysis was used to synthesize cytochalasin B-like compounds and inhibition of glucose uptake in cancer cells was demonstrated.

Cited by 11 publications

References 39 publications

New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems

New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems

Polyenals and Polyenones in Aminocatalysis: A Decade Building Complex Frameworks from Simple Blocks

Synthesis and migrastatic activity of cytochalasin analogues lacking a macrocyclic moiety

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