Literature DB >> 17036106

First total synthesis of the 7-oxygenated carbazole alkaloids clauszoline-K, 3-formyl-7-hydroxycarbazole, clausine M, clausine N and the anti-HIV active siamenol using a highly efficient palladium-catalyzed approach.

Micha P Krahl1, Anne Jäger, Tilo Krause, Hans-Joachim Knölker.   

Abstract

Using a convergent palladium-catalyzed construction of the carbazole framework as the key step we have achieved a short synthesis of the 7-oxygenated carbazole alkaloids clauszoline-K, 3-formyl-7-hydroxycarbazole, clausine C (clauszoline-L), clausine M, clausine N and the anti-HIV active siamenol.

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Year:  2006        PMID: 17036106     DOI: 10.1039/b607792g

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


  6 in total

Review 1.  Synthesis of indole derivatives as prevalent moieties present in selected alkaloids.

Authors:  Majid M Heravi; Zahra Amiri; Kosar Kafshdarzadeh; Vahideh Zadsirjan
Journal:  RSC Adv       Date:  2021-10-15       Impact factor: 4.036

2.  Rh(2)(II)-catalyzed synthesis of carbazoles from biaryl azides.

Authors:  Benjamin J Stokes; Brankica Jovanović; Huijun Dong; Kathleen J Richert; Ryan D Riell; Tom G Driver
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

3.  Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.

Authors:  W C Peter Tsang; Rachel H Munday; Gordon Brasche; Nan Zheng; Stephen L Buchwald
Journal:  J Org Chem       Date:  2008-08-29       Impact factor: 4.354

4.  Construction of highly functionalized carbazoles via condensation of an enolate to a nitro group.

Authors:  Tej Narayan Poudel; Yong Rok Lee
Journal:  Chem Sci       Date:  2015-09-16       Impact factor: 9.825

5.  Synthesis and Activity against Mycobacterium tuberculosis of Olivacine and Oxygenated Derivatives.

Authors:  Ulrike Schmidt; Gabriele Theumer; Anne Jäger; Olga Kataeva; Baojie Wan; Scott G Franzblau; Hans-Joachim Knölker
Journal:  Molecules       Date:  2018-06-09       Impact factor: 4.411

6.  Palladium-catalyzed synthesis of natural and unnatural 2-, 5-, and 7-oxygenated carbazole alkaloids from N-arylcyclohexane enaminones.

Authors:  Rafael Bautista; Pablo A Montoya; Araceli Rebollar; Eleuterio Burgueño; Joaquín Tamariz
Journal:  Molecules       Date:  2013-08-26       Impact factor: 4.411

  6 in total

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