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Literature DB >> 20856944

Facile nucleophilic substitution at the C3a tertiary carbon of the 3a-bromohexahydropyrrolo[2,3-b]indole scaffold.

Isabel Villanueva-Margalef¹, David E Thurston, Giovanna Zinzalla.

Abstract

The synthesis of 3a-substituted hexahydropyrrolo[2,3-b]indole derivatives via nucleophilic substitution at the C3a position is reported. Nitrogen-, oxygen-, sulfur-, fluoro- and carbon-based nucleophiles have been employed, using both conventional organic solvents and ionic liquids. The C3a-substituted derivatives were obtained in good to excellent yields.

Entities: Chemical Gene

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Year: 2010 PMID： 20856944 DOI： 10.1039/c0ob00327a

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

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Cited

7 in total

1. Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors: Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal: J Am Chem Soc Date: 2016-01-19 Impact factor: 15.419

2. Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

Authors: Stephen P Lathrop; Mohammad Movassaghi
Journal: Chem Sci Date: 2014-01-01 Impact factor: 9.825

3. Lewis Acid Catalyzed Displacement of Trichloroacetimidates in the Synthesis of Functionalized Pyrroloindolines.

Authors: Arijit A Adhikari; John D Chisholm
Journal: Org Lett Date: 2016-08-03 Impact factor: 6.005

4. 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

Facile nucleophilic substitution at the C3a tertiary carbon of the 3a-bromohexahydropyrrolo[2,3-b]indole scaffold.

1. Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

2. Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

3. Lewis Acid Catalyzed Displacement of Trichloroacetimidates in the Synthesis of Functionalized Pyrroloindolines.

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

5. Concise Total Synthesis of (+)-Gliocladins B and C.

6. Concise Total Synthesis of (+)-Bionectins A and C.

7. Concise total synthesis of (+)-asperazine A and (+)-pestalazine B.