Total synthesis of (±)-parvifoline and (±)-isoparvifolinone

Villagómez-Ibarra, Roberto; Álvarez-Cisneros, Celina; Joseph‐Nathan, Pedro

doi:10.1016/0040-4020(95)00517-c

Cited by 20 publications

(12 citation statements)

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“…The inhibitory effect of colchicine was evaluated in the polymerization experiments using different concentrations. It was observed that at 100 μM the amount of colchicine was sufficient to fully inhibit polymerization after 30 min, at 50 μM colchicine polymerization inhibition prevails by 94%, while at 10 and 5 μM the phases of polymerization 22 could be observed more clearly with inhibition of 48% and 37%, respectively (Supporting 6), 13,14-epoxyparvifoline (7), and 8,12-oxyparvifoline (9) and molecular model of 8,14-oxyparvifoline (11). Information, Figure S39).…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

“…Figure 4. X-ray diffraction structures of 12,13-epoxyparvifoline benzoate (6), 13,14-epoxyparvifoline(7), and 8,12-oxyparvifoline(9) and molecular model of 8,14-oxyparvifoline(11).…”

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confidence: 99%

“…oolepis . Compound 1 and some analogues have been the subject of several synthetic protocols − that have overcome the challenge of the eight-membered-ring formation. The chemical structure of parvifoline ( 1 ) shares some molecular features with colchicine, a representative inhibitor of tubulin polymerization .…”

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confidence: 99%

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Parvifoline Derivatives as Tubulin Polymerization Inhibitors

et al. 2019

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A series of functionalized sesquiterpenoids derived from benzocyclooctene, including natural parvifoline (1), isoparvifoline (3), epoxyparvifoline (5), epoxyisoparvifoline (7), 8,12-oxyparfivoline (9), 8,14-oxyparvifoline (11), and the respective benzoyl derivatives 2, 4, 6, 8, 10, and 12, were prepared and tested for their inhibitory effect on the in vitro α,β-tubulin polymerization process. The structural analysis and characterization of the new compounds 5–7 and 9–12 were achieved by 1D and 2D NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis of 6, 7, and 9. Preparation of 9 and 12 involved molecular rearrangements of the epoxide group with transannular 1,5-hydride shifts. At 10 μM compounds 1, 5, and 8 inhibited the polymerization of the α,β-tubulin heterodimer by 24%, 49%, and 90% as compared to colchicine. These compounds were subjected to docking analysis that supported their interactions in a colchicine binding site located in the α-tubulin subunit, in the pocket formed by Phe296, Pro298, Pro307, His309, Tyr312, Lys338, Thr340, Ile341, and Gln342. Competitive inhibition assays with colchicine were also performed for the three compounds, which supported their binding at the colchicine secondary site in α-tubulin. Also, evaluations of their cytotoxicity on MCF7 breast carcinoma, HeLa cervix carcinoma, and HCT 116 colon carcinoma cell lines were carried out and showed that 8 is active against the HeLa and HCT 116 cell lines with IC50 3.3 ± 0.2 and 5.0 ± 0.5 μM, respectively.

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Section: Journal Of Natural Productsmentioning

confidence: 99%

“…Figure 4. X-ray diffraction structures of 12,13-epoxyparvifoline benzoate (6), 13,14-epoxyparvifoline(7), and 8,12-oxyparvifoline(9) and molecular model of 8,14-oxyparvifoline(11).…”

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Parvifoline Derivatives as Tubulin Polymerization Inhibitors

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“…In diesem Zusammenhang liegt der wichtigste Anwendungsbereich von C‐C‐Fragmentierungen. Der funktionalisierte achtgliedrige Ring von Parvifolin ( 330 ) und Isoparvifolinon ( 331 ) wurde durch eine Ringerweiterung über Fragmentierung aus dem racemischen trans ‐Hydroxymesylat 328 konstruiert (Schema ) 155. Das Z ‐Olefin 329 wurde dann für einen Zugang zu beiden Sesquiterpenen weiterentwickelt.…”

Section: Fortschritt Und Anwendungenunclassified

“… Schlüsselfragmentierungen in Joseph‐Nathans Synthesen von (±)‐Parvifolin ( 330 ) und (±)‐Isoparvifolinon ( 331 ) (1995) 155…”

Section: Fortschritt Und Anwendungenunclassified

C‐C‐Fragmentierung: Herkunft und jüngste Anwendungen

2013

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Sechzig Jahre sind vergangen, seit Eschenmoser und Frey den Archetyp der C‐C‐Fragmentierung beschrieben. Rasch folgten neue Fragmentierungen und mehrere Varianten des Originals. Viele dieser Variationen, einschließlich der Beckmann‐, Grob‐, Wharton‐, Marshall‐ und der Eschenmoser‐Tanabe‐Fragmentierungen, sowie weiteren, wurden im Laufe der Jahre in Übersichten besprochen, eine genaue Untersuchung des Ursprungs von Fragmentierungen steht aber noch aus. Vor kurzem tauchten neue nützliche Methoden auf, insbesondere Fragmentierungen, die zu Alkinen und Allenen führen, und solche Reaktionen wurden auf eine Reihe an komplexen Leitmotiven und Naturstoffe angewendet. Dieser Aufsatz verfolgt die Entwicklung der Fragmentierungen und bietet eine Zusammenfassung der Methoden, Anwendungen und neue Einblicke in heterolytische C‐C‐Fragmentierungen der letzten zwanzig Jahre.

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Forging Medium Rings via I(I)/I(III)‐Catalyzed Diene Carbofunctionalization

Häfliger

Wang

et al. 2023

Angewandte Chemie

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A main‐group catalysis‐based strategy to access 8‐membered carbocycles via the direct carbofunctionalization of 2‐phenethyl‐substituted 1,3‐dienes is disclosed. Through the intervention of an I(I)/I(III) catalysis cycle, the synthesis of densely functionalized, fluorinated benzocyclooctenes can be achieved in an operationally simple manner. Modulating the oxidation / activation regime, and the external nucleophile, the process has been extended to unify the challenging cyclization with formation of allylic C‐O, C‐N, and C‐C bonds (>30 examples). Derivatization of the product benzocyclooctenes is demonstrated together with X‐ray conformational analysis, preliminary validation of enantioselective catalysis and a scalable resolution protocol.

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Total synthesis of (±)-parvifoline and (±)-isoparvifolinone

Cited by 20 publications

References 20 publications

Parvifoline Derivatives as Tubulin Polymerization Inhibitors

Parvifoline Derivatives as Tubulin Polymerization Inhibitors

C‐C‐Fragmentierung: Herkunft und jüngste Anwendungen

Forging Medium Rings via I(I)/I(III)‐Catalyzed Diene Carbofunctionalization

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