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Literature DB >> 29663602

Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-Lundurine A.

Aaron Nash¹, Xiangbing Qi¹, Pradip Maity¹, Kyle Owens¹, Uttam K Tambar¹.

Abstract

A novel vinylogous Pictet-Spengler cyclization has been developed for the generation of indole-annulated medium-sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a prevalent structural motif in many biologically active alkaloids. The strategy has been applied to the total synthesis of (±)-lundurine A.

Entities: Chemical Disease Gene Species

Keywords: Lewis acids; alkaloids; cyclization; nitrogen heterocycles; total synthesis

Mesh：

Substances：

Year: 2018 PMID： 29663602 PMCID： PMC6392010 DOI： 10.1002/anie.201803702

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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References

29 in total

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Authors: R Nishanth Rao; Barnali Maiti; Kaushik Chanda
Journal: ACS Comb Sci Date: 2017-03-17 Impact factor: 3.784

Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-Lundurine A.

1. Highly enantioselective catalytic acyl-pictet-spengler reactions.

2. Chemoselective N-acylation of indoles and oxazolidinones with carbonylazoles.

3. Enantioselective friedel-crafts reaction of electron-rich alkenes catalyzed by chiral Brønsted acid.

4. A multimetallic piano-stool Ir-Sn3 catalyst for nucleophilic substitution reaction of γ-hydroxy lactams through N-acyliminium ions.

Review 5. Application of Pictet-Spengler Reaction to Indole-Based Alkaloids Containing Tetrahydro-β-carboline Scaffold in Combinatorial Chemistry.

6. A concise and versatile synthesis of alkaloids from Kopsia tenuis: total synthesis of (±)-lundurine A and B.

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9. Total synthesis of (±)-lundurine B.

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