Synthese von entzündungshemmenden α‐Arylalkansäuren durch 1,2‐Arylverschiebung

Giordano, Claudio; Castaldi, Graziano; Uggeri, Fulvio

doi:10.1002/ange.19840960606

Cited by 21 publications

(11 citation statements)

References 32 publications

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“…A key step in the synthesis of tricyclic compound 381 was the pinacol‐type ketal rearrangement of mesylate 378 to give α‐aryl ester 380 , involving migration of the electron‐rich aryl ring (with inversion of stereochemistry at the C9 position) via bridged phenonium ion 379 . This type of rearrangement, initially developed by Tsuchihashi and co‐workers,207 provides a potentially useful stereocontrolled entry to the α‐aryl alkanoic acid class of compounds, which includes the widely used nonsteroidal anti‐inflammatory drugs ibuprofen ( 386 ) and naproxen ( 387 ) shown in Scheme 52 b 208…”

Section: Pericyclic Cascadesmentioning

confidence: 99%

Cascade Reactions in Total Synthesis

2006

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The design and implementation of cascade reactions is a challenging facet of organic chemistry, yet one that can impart striking novelty, elegance, and efficiency to synthetic strategies. The application of cascade reactions to natural products synthesis represents a particularly demanding task, but the results can be both stunning and instructive. This Review highlights selected examples of cascade reactions in total synthesis, with particular emphasis on recent applications therein. The examples discussed herein illustrate the power of these processes in the construction of complex molecules and underscore their future potential in chemical synthesis.

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Section: Pericyclic Cascadesmentioning

confidence: 99%

Cascade Reactions in Total Synthesis

2006

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“…Dabei wanderte der elektronenreiche Arenring, und es entstand das überbrückte Phenoniumion 379 unter Inversion der Konfiguration an C9. Diese Umlagerung, die von Tsuchihashi et al207 entwickelt wurde, liefert einen stereoselektiven Zugang zu α‐Arylalkansäuren, zu denen auch die häufig eingesetzten nichtsteroiden Entzündungshemmer Ibuprofen ( 386 ) und Naproxen ( 387 ) zählen (Schema 52 b) 208…”

Section: Pericyclische Kaskadenunclassified

Kaskadenreaktionen in der Totalsynthese

2006

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Die Entwicklung und Umsetzung von Kaskadenreaktionen hat zu beachtlichen neuartigen, eleganten und effizienten Synthesestrategien geführt. Als besonders anspruchsvoll erwies sich die Anwendung von Kaskadenreaktionen in der Naturstoffsynthese, doch gerade hier winken verblüffende und zugleich aufschlussreiche Ergebnisse als Belohnung. In diesem Aufsatz werden ausgewählte Kaskadenreaktionen in der Totalsynthese erläutert, wobei neuere Anwendungen besonders hervorgehoben werden. Die erörterten Beispiele sollen die Leistungsfähigkeit dieser Prozesse beim Aufbau von komplexen Molekülstrukturen veranschaulichen und ihr Potenzial für zukünftige chemische Synthesen verdeutlichen.

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“…A new simple approach to a-alkylphenylacetic acids, which are important as antipyretics and insecticides of the pyrethroid type, [38] is particularly attractive. Examples are the high-yield syntheses of ibuprofen 59a and naproxene is an advantage offered by only few reactions, in particular sextet rearrangements.…”

Section: Preparative Applicationmentioning

confidence: 99%

The Isocyanide–Cyanide Rearrangement; Mechanism and Preparative Applications

Rüchardt

Meier

Haaf

et al. 1991

Angew. Chem. Int. Ed. Engl.

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The cover picture (center) shows a CPK model of the structure of a hemicarcerand-a global minimum calculated with the MM2 force field (with the phenylethyl groups omitted). Quite astounding transformations have been carried out in its cavity. Reactions that occur within the host are gold-colored and the one that occurs outside is blue. The golden orb in the middle shows the locations of the guests within the hemicarcerand and highlights the small portal through which the guests enter and exit the interior of the host. "Incarcerated" cyclobutadiene is stable at room temperature and above in the absence of oxygen, but reacts with oxygen that enters the "container" to give incarcerated maleinaldehyde. This new type of chemistry promises to open a whole new field involving the study of electronically and sterically unperturbed reactive species. Review Art icl esOptically active cyanides (l), which are synthetically useful building blocks, may be obtained from naturally occurring a-amino acids (2) in overall yields of up to 60% and with ee values of > 98%. The key feature of the approach discussed here is the isocyanide rearrangement of 3, induced by flash photolysis. Thus this rearrangement, which has long been investigated primarily in terms of mechanism, now constitutes one step in a preparatively useful procedure.

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Synthese von entzündungshemmenden α‐Arylalkansäuren durch 1,2‐Arylverschiebung

Cited by 21 publications

References 32 publications

Cascade Reactions in Total Synthesis

Cascade Reactions in Total Synthesis

Kaskadenreaktionen in der Totalsynthese

The Isocyanide–Cyanide Rearrangement; Mechanism and Preparative Applications

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