Asymmetric, stereocontrolled total synthesis of (+) and (−)-spirotryprostatin B via a diastereoselective azomethine ylide [1,3]-dipolar cycloaddition reaction

Sebahar, Paul R.; Osada, Hiroyuki; Usui, Takeo; Williams, Robert M.

doi:10.1016/s0040-4020(02)00630-0

Cited by 93 publications

(49 citation statements)

References 71 publications

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“…Williams et al proposed another method of spirotryprostatin B 15 synthesis based on the asymmetric 1,3-dipolar cycloaddition of a generated in situ chiral azomethine ylide 85 to the ethyl oxindolylidene acetate 82 (Scheme 16) [59].…”

Section: 3-dipolar Cycloaddition Reactions In the Synthesis Of Spirmentioning

confidence: 99%

Molecular diversity of spirooxindoles. Synthesis and biological activity

et al. 2015

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Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications. This review focuses on the various strategies for the enantioselective synthesis of spirocyclic oxindoles relying on reports over the past decade and from earlier work. The spirooxindoles in this review are separated into three structural classes, and then further categorized into the method type from which the spirocycle is generated.

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Section: 3-dipolar Cycloaddition Reactions In the Synthesis Of Spirmentioning

confidence: 99%

Molecular diversity of spirooxindoles. Synthesis and biological activity

et al. 2015

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“…Reac-tion with oxindole 43 led to cycloadduct 45 in 82% yield (Scheme 14). [41,42] Scheme 14. Key transformation in Williams' synthesis of spirotryprostatin B…”

Section: Dipolar Cycloaddition Reactionsmentioning

confidence: 99%

Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids

2003

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The spiro[pyrrolidine‐3,3′‐oxindole] ring system is found at the core of a number of alkaloids, which possess significant biological activity and are interesting, challenging targets for chemical synthesis. In the present review, we report on the different strategies for the synthesis of the spiro[pyrrolidine‐3,3′‐oxindole] ring system in the context of recent synthesis of coerulescine, horsfiline, elacomine, salacin, pteropodine, alstonisine, spirotryprostatin A and B, and strychnofoline. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…[23] Der sehr elegante Zugang nutzt eine Dreikomponentenreaktion (3-CR) von Morpholinon 31, Aldehyd 32 und Oxindolylidenacetat 33 zum Aufbau der Spirooxindol-Kernstruktur (Schema 5). 31 und 32 bilden ein chirales Azomethinylid mit E-Konfiguration, das eine bereitwillig ablaufende [3+2]-Cycloaddition mit dem Dipolarophil 33 eingeht und das Cycloaddukt 34 liefert.…”

Section: Asymmetrische 13-dipolare Cycloadditionunclassified

Natürliche Pyrrolidinylspirooxindole als Vorlagen für die Entwicklung medizinischer Wirkstoffe

Galliford¹,

Scheidt²

2007

Angewandte Chemie

515

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Das 3,3′‐Pyrrolidinylspirooxindol‐System ist ein privilegiertes heterocyclisches Strukturmotiv, das die zentrale Einheit bei einer großen Familie von natürlichen Alkaloiden mit starken Bioaktivitätsprofilen und interessanten Struktureigenschaften bildet. Neue bedeutende Fortschritte bei der Synthese dieses kondensierten heterocyclischen Systems haben ein starkes Interesse an der Entwicklung verwandter Verbindungen als mögliche Wirkstoffe oder biologische Sonden hervorgerufen.

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Asymmetric, stereocontrolled total synthesis of (+) and (−)-spirotryprostatin B via a diastereoselective azomethine ylide [1,3]-dipolar cycloaddition reaction

Cited by 93 publications

References 71 publications

Molecular diversity of spirooxindoles. Synthesis and biological activity

Molecular diversity of spirooxindoles. Synthesis and biological activity

Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids

Natürliche Pyrrolidinylspirooxindole als Vorlagen für die Entwicklung medizinischer Wirkstoffe

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