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Literature DB >> 15228262

Combined directed ortho and remote metalation-cross-coupling strategies. General method for benzo[a]carbazoles and the synthesis of an unnamed indolo[2,3-a]carbazole alkaloid.

Abstract

[reaction: see text] An efficient route to benzo[a]carbazoles via a metalation-cross-coupling sequence has been demonstrated and its application to the synthesis of the antitumor and antiviral alkaloid 6-cyano-5-methoxy-12-methylindolo[2,3-a]carbazole has been achieved.

Entities: Chemical

Mesh：

Substances：

Year: 2004 PMID： 15228262 DOI： 10.1021/ol049780x

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

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Cited

6 in total

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

Authors: Sunkyu Han; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal: J Org Chem Date: 2013-10-31 Impact factor: 4.354

2. Natural product leads for drug discovery: isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents.

Authors: Songpo Guo; Suresh K Tipparaju; Scott D Pegan; Baojie Wan; Shunyan Mo; Jimmy Orjala; Andrew D Mesecar; Scott G Franzblau; Alan P Kozikowski
Journal: Bioorg Med Chem Date: 2009-09-04 Impact factor: 3.641

3. Direct C7 Functionalization of Tryptophan. Synthesis of Methyl (S)-2-((tert-Butoxycarbonyl)amino)-3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate.

Authors: Kazuma Amaike; Richard P Loach; Mohammad Movassaghi
Journal: Organic Synth Date: 2015

Combined directed ortho and remote metalation-cross-coupling strategies. General method for benzo[a]carbazoles and the synthesis of an unnamed indolo[2,3-a]carbazole alkaloid.

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

2. Natural product leads for drug discovery: isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents.

3. Direct C7 Functionalization of Tryptophan. Synthesis of Methyl (S)-2-((tert-Butoxycarbonyl)amino)-3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate.

4. On the control of secondary carbanion structure utilising ligand effects during directed metallation.

5. C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

6. Synthesis of 2-BMIDA Indoles via Heteroannulation: Applications in Drug Scaffold and Natural Product Synthesis.