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Literature DB >> 18722452

Stereoselective oxidative rearrangement of 2-aryl tryptamine derivatives.

Mohammad Movassaghi¹, Michael A Schmidt, James A Ashenhurst.

Abstract

The oxidation of 2-aryl tryptamines followed by a stereoselective rearrangement provides a versatile strategy for the synthesis of C3-quaternary oxindoles bearing a C3-aryl group. Treatment of optically active 2-aryl hydroxyindolenines with scandium trifluoromethanesulfonate in toluene at 110 degrees C leads to complete and stereoselective isomerization to the corresponding C3-aryl oxindoles which represent versatile intermediates for the synthesis of C3a-aryl hexahydropyrroloindoles.

Entities: Chemical

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Year: 2008 PMID： 18722452 DOI： 10.1021/ol8015176

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

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Cited

15 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. 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

Stereoselective oxidative rearrangement of 2-aryl tryptamine derivatives.

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

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

3. Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines.

4. A green non-acid-catalyzed process for direct N=N-C group formation: comprehensive study, modeling, and optimization.

5. Concise total synthesis and stereochemical revision of all (-)-trigonoliimines.

6. A cycloisomerization/Friedel-Crafts alkylation strategy for the synthesis of pyrano[3,4-b]indoles.

7. Electrophilic Oxidation and [1,2]-Rearrangement of the Biindole Core of Birinapant.

8. Copper-catalyzed diastereoselective arylation of tryptophan derivatives: total synthesis of (+)-naseseazines A and B.

9. Electrophilic Carbonyl Activation: Competing Condensative Cyclizations of Tryptamine Derivatives.

10. Chemoselective and enantioselective oxidation of indoles employing aspartyl peptide catalysts.