Synthesis and cyclisation of didemnimide C and its imidazol-1-yl isomer

Terpin, Andreas; Winklhofer, Christian; Schumann, Susanne; Steglich, Wölfgang

doi:10.1016/s0040-4020(97)10410-0

Cited by 49 publications

(34 citation statements)

References 17 publications

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“…Among these, compounds of general structure 4 are potent tyrosine-kinase inhibitors, [1] and compound 5 is very close to synthetic analogs of staurosporine. [2,3] Scheme 1…”

Section: Introductionmentioning

confidence: 99%

A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives

Boisbrun¹,

Jeannin²,

Toupet

et al. 2000

Eur. J. Org. Chem.

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Condensation between indole, Meldrum’s acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a−c. The latter were cyclized to indole‐substituted 2‐pyrrolidones 15a−b or 3‐aminopyrrolid‐2‐ones 18a−b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3′,4′:5,6]pyrido[3,4‐b]indol‐3(2H)‐ones 19a and 20a by a Pictet−Spengler condensation with benzaldehyde.

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“…Among these, compounds of general structure 4 are potent tyrosine-kinase inhibitors, [1] and compound 5 is very close to synthetic analogs of staurosporine. [2,3] Scheme 1…”

Section: Introductionmentioning

confidence: 99%

A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives

Boisbrun¹,

Jeannin²,

Toupet

et al. 2000

Eur. J. Org. Chem.

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“…Synthesis of 3,4-bisindolylmaleimides according to Steglich et al [16] Scheme 2. Synthesis of 3,4-bisarylmaleimides according to Faul et al [17] Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

“…[14] Due to their attractive properties, several research groups have synthesized 3-indolo-substituted maleimides. [15] The most widely used synthetic approaches were developed by the groups of Steglich [16] and Faul [17] (Schemes 1 and 2). According to the Steglich procedure, indolyl magnesium bromide is reacted with 3,4-dibromomaleimide to give monoor disubstituted products depending on the ratio of the starting materials.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Biologically Interesting 3,4‐Diaryl‐Substituted Succinimides and Maleimides: Application of Iron‐Catalyzed Carbonylations

Prateeptongkum

Driller

Jackstell

et al. 2010

Chemistry A European J

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A straightforward two-step synthesis of trans-3,4-disubstituted succinimides through a palladium-catalyzed Sonogashira reaction and an iron-catalyzed double carbonylation is described. In situ oxidative dehydrogenation gave the corresponding 3,4-diarylmaleimides. By starting from readily available aryl and heteroaryl halides, a variety of new analogues and derivatives of bioactive 3,4-bisindolylmaleimides are obtained in good yield and selectivity.

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“…Other examples of Stille couplings using 2-substituted 5-stannylimidazoles [290] are applicable to the synthesis of cytotoxic agents [291] and an imidazolyl isomer of the alkaloid didemnimide C [292]. 5-Stannylimidazoles have also been prepared by a 2,5-dilithiation, followed by a double stannylation and a 2-hydrodestannylation sequence [291].…”

Section: Stille Cross-coupling Reactionsmentioning

confidence: 99%