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Literature DB >> 18069844

Mechanistic insights into the stereocontrolled synthesis of hexahydropyrrolo[2,3-b]indoles by electrophilic activation of tryptophan derivatives.

Carlos Silva López¹, Carlos Pérez-Balado, Paula Rodríguez-Graña, Angel R de Lera.

Abstract

A three-step mechanism involving the formation and rearrangement of an intermediate with indoline-azetidine spirocyclic core structure was shown by DFT computations to account for the electrophilic cyclization of tryptophan derivatives to hexahydropyrrolo[2,3-b]indoles. The corresponding 3a-bromo derivatives have been obtained in high yields and synthetically useful exo/endo ratios.

Entities: Chemical Gene

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Year: 2007 PMID： 18069844 DOI： 10.1021/ol702732j

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors: Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal: J Am Chem Soc Date: 2010-05-26 Impact factor: 15.419

2. Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors: Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal: Angew Chem Int Ed Engl Date: 2011-07-12 Impact factor: 15.336

3. Straightforward Access to Hexahydropyrrolo[2,3-b]indole Core by a Regioselective C3-Azo Coupling Reaction of Arenediazonium Compounds with Tryptamines.

Authors: David E Stephens; Oleg V Larionov
Journal: European J Org Chem Date: 2014-06-01

Mechanistic insights into the stereocontrolled synthesis of hexahydropyrrolo[2,3-b]indoles by electrophilic activation of tryptophan derivatives.

1. Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

2. Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

3. Straightforward Access to Hexahydropyrrolo[2,3-b]indole Core by a Regioselective C3-Azo Coupling Reaction of Arenediazonium Compounds with Tryptamines.

4. Total synthesis guided structure elucidation of (+)-psychotetramine.

5. Palladium-Catalyzed, Enantioselective Desymmetrization of N-Acylaziridines with Indoles.

6. On the prevalence of bridged macrocyclic pyrroloindolines formed in regiodivergent alkylations of tryptophan.

7. Total Synthesis of the Proposed Structure of (-)-Novofumigatamide, Isomers Thereof, and Analogues. Part I.