Studies on the synthesis of the antitumor agent CC-1065. Synthesis of the unprotected cyclopropapyrroloindole A portion using the 3,3'-bipyrrole strategy

Magnus, Philip; Gallagher, Timothy; Schultz, James T.; Or, Yat Sun; Ananthanarayan, T. P.

doi:10.1021/ja00243a025

Cited by 62 publications

(12 citation statements)

References 1 publication

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“…As shown in Scheme 3 , the electron-withdrawing groups may be esters, amides, ketones, nitros, cyanos, aryls, etc. [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 ]. Based on the different types of electron-withdrawing group attached to the alkenes, they are classified and described in order ( Scheme 3 ).…”

Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Zhang

2018

Molecules

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Pyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core framework in many pharmaceutical and natural product structures, some of which have good biological activities. The Van Leusen [3+2] cycloaddition reaction based on tosylmethyl isocyanides (TosMICs) and electron-deficient compounds as a substrate, which has been continuously developed due to its advantages such as operationally simple, easily available starting materials, and broadly range of substrates, is one of the most convenient methods to synthetize pyrrole heterocycles. In this review, we discuss the different types of two carbon synthons in the Van Leusen pyrrole reaction and give a summary of the progress of these synthesis methods in the past two decades.

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Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Zhang

2018

Molecules

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“…Crystal data was obtained by a Bruker SMART X-Ray single crystal diffractometer (Bruker, Germany). The substrates ( E )-3-methyl-4-nitro-5-styrylisoxazoles 2 were prepared by a similar method as reported papers [ 49 , 50 ]. More informations can be found in the supplementary materials .…”

Section: Methodsmentioning

confidence: 99%

[3+2] Cycloaddition of Tosylmethyl Isocyanide with Styrylisoxazoles: Facile Access to Polysubstituted 3-(Isoxazol-5-yl)pyrroles

Zhang

2017

Molecules

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A facile access to polysubstituted 3-(isoxazol-5-yl)pyrroles was developed through [3+2] cycloaddition of tosylmethyl isocyanide (TosMIC) and styrylisoxazoles. In the presence of KOH, various styrylisoxazoles reacted smoothly with tosylmethyl isocyanide and analogs to deliver a wide range of 3-(isoxazol-5-yl)pyrroles at ambient temperature. This transformation is operationally simple, high-yielding, and displays broad substrate scope.

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“…Die Umsetzung der Hydroxamsaure 30 mit iiberschussigem Vinyl-acetat in Gegenwart einer katalytischen Menge Li,PdCl, und unter Zusatz von DMSO erbrachte das gesuchte tricyclische System 31. Die selektive Reduktion der einen Indol-(C=C)-Bindung") unter gleichzeitiger Entfernung der Bn-Gruppe fuhrte zum bekannten [30] Zur Diskussion dieser Redoxreaktion, d.h. der Oxidation des 2,3-Dihydro-1H-indols zum Indol unter gleichzeitiger (N-0)-Spaitung der Hydroxylamino-Gruppe, vgl. weiter unten.…”

Section: R = B~ X = B R T Lunclassified

Der Zugang zum Antitumor‐Antibiotikum CC‐1065 mittels Hetero‐Cope‐Umlagerung von Vinyl‐N‐phenylhydroxamaten

Martin

1989

Helvetica Chimica Acta

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The Access to the Three Subunits of the Antitumor Antibiotic CC-1065 by Hetero-Cope Rearrangement of Vinyl N-PhenylhydroxamatesThe use of the hetero-Cope rearrangement of vinyl N-phenylhydroxamates to indoles for the preparation of the 1,2-dihydro-3H,6H-benzo[1,2-b :4,3-b']dipyrrole skeleton, the structural subunits characteristic of the antitumor antibiotic CC-1065 as well as the phosphodiesterase inhibitors PDE-I and PDE-II is described.

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Studies on the synthesis of the antitumor agent CC-1065. Synthesis of the unprotected cyclopropapyrroloindole A portion using the 3,3'-bipyrrole strategy

Cited by 62 publications

References 1 publication

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

[3+2] Cycloaddition of Tosylmethyl Isocyanide with Styrylisoxazoles: Facile Access to Polysubstituted 3-(Isoxazol-5-yl)pyrroles

Der Zugang zum Antitumor‐Antibiotikum CC‐1065 mittels Hetero‐Cope‐Umlagerung von Vinyl‐N‐phenylhydroxamaten

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