Unprecedented stereospecific synthesis of a novel tetracyclic ring system, a hybrid of tetrahydropyrrolo[2,3-b]indole and tetrahydroimidazo[1,2-a]indole, via a domino reaction upon a tryptophan-derived amino nitrile.

doi:10.1021/OL049222I

Paper

Unprecedented stereospecific synthesis of a novel tetracyclic ring system, a hybrid of tetrahydropyrrolo[2,3-b]indole and tetrahydroimidazo[1,2-a]indole, via a domino reaction upon a tryptophan-derived amino nitrile.

Published 2004 · Juan A González-Vera, M Teresa García-López, Rosario Herranz

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Abstract

Compounds containing a novel tetracyclic ring system, a hybrid of tetrahydropyrrolo[2,3-b]indole and tetrahydroimidazo[1,2-a]indole, are synthesized via an acid-mediated stereospecific domino tautomerization of a tryptophan-derived alpha-amino nitrile. Characterization of these new compounds and preliminary studies on the reactivity of the tetracyclic heterocyclic system are reported. [reaction: see text]

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This study demonstrates the first stereospecific synthesis of a novel tetracyclic ring system, a hybrid of tetrahydropyrrolo[2,3-b]indole and tetrahydroimidazo[1,2-a]indole, using a

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Unprecedented stereospecific synthesis of a novel tetracyclic ring system, a hybrid of tetrahydropyrrolo[2,3-b]indole and tetrahydroimidazo[1,2-a]indole, via a domino reaction upon a tryptophan-derived amino nitrile.

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Citations

Tricyclic Imidazolidin-4-ones by Witkop Oxidation of Tetrahydro-β-carbolines.

Tricyclic imidazolidin-4-ones can be synthesized from 1,1-disubstituted tetrahydro-beta-carbolines with high diastereoselectivity, expanding the menu of tetrahydro-beta-carbol

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8-Lipoxygenase catalyzes oxygenation of poly-unsaturated fatty acids with precise regio- and stereo-selectivity, influenced by substrate conformational dynamics and oxygen transport network.

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This study presents a modular and versatile method for the synthesis of C4-substituted tryptophan derivatives, enabling rapid access to the tricyclic azepino indole skeleton in natural products.

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