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Literature DB >> 23909946

Platinum-catalyzed tandem indole annulation/arylation for the synthesis of diindolylmethanes and indolo[3,2-b]carbazoles.

Dongxu Shu¹, Gabrielle N Winston-McPherson, Wangze Song, Weiping Tang.

Abstract

Various diindolylmethanes were prepared from propargylic ethers and substituted indoles via a platinum-catalyzed tandem indole annulation/arylation cascade. The resulting diindolylmethanes could be converted to natural product malassezin by formylation or indolo[3,2-b]carbazoles by cyclization.

Entities: Chemical Disease Gene

Mesh：

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Year: 2013 PMID： 23909946 PMCID： PMC3776426 DOI： 10.1021/ol4018408

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

27 in total

Review 1. Isolation and synthesis of biologically active carbazole alkaloids.

Authors: Hans-Joachim Knölker; Kethiri R Reddy
Journal: Chem Rev Date: 2002-11 Impact factor: 60.622

2. Cationic ruthenium(II) catalysts for oxidative C-H/N-H bond functionalizations of anilines with removable directing group: synthesis of indoles in water.

Authors: Lutz Ackermann; Alexander V Lygin
Journal: Org Lett Date: 2012-01-13 Impact factor: 6.005

Review 3. Progress in palladium-based catalytic systems for the sustainable synthesis of annulated heterocycles: a focus on indole backbones.

Authors: Mélanie Platon; Régine Amardeil; Laurent Djakovitch; Jean-Cyrille Hierso
Journal: Chem Soc Rev Date: 2012-03-26 Impact factor: 54.564

Review 4. Potential protective mechanisms of aryl hydrocarbon receptor (AHR) signaling in benign prostatic hyperplasia.

Authors: Vatsal Mehta; Chad M Vezina
Journal: Differentiation Date: 2011 Nov-Dec Impact factor: 3.880

5. Recent advances in indole syntheses: new routes for a classic target.

Authors: Rubén Vicente
Journal: Org Biomol Chem Date: 2011-07-21 Impact factor: 3.876

6. Palladium(II)-catalyzed tandem cyclization/C-H functionalization of alkynes for the synthesis of functionalized indoles.

Authors: Xiao-Feng Xia; Ning Wang; Lu Lu Zhang; Xian-Rong Song; Xue-Yuan Liu; Yong-Min Liang
Journal: J Org Chem Date: 2012-09-27 Impact factor: 4.354

7. Synthesis of N-azolylindoles by copper-catalyzed C-H/N-H coupling-annulation sequence of o-alkynylanilines.

Authors: Yoshiro Oda; Koji Hirano; Tetsuya Satoh; Masahiro Miura
Journal: Org Lett Date: 2012-01-11 Impact factor: 6.005

8. Exogenous stimuli maintain intraepithelial lymphocytes via aryl hydrocarbon receptor activation.

Authors: Ying Li; Silvia Innocentin; David R Withers; Natalie A Roberts; Alec R Gallagher; Elena F Grigorieva; Christoph Wilhelm; Marc Veldhoen
Journal: Cell Date: 2011-10-13 Impact factor: 41.582

9. Control of T(reg) and T(H)17 cell differentiation by the aryl hydrocarbon receptor.

Authors: Francisco J Quintana; Alexandre S Basso; Antonio H Iglesias; Thomas Korn; Mauricio F Farez; Estelle Bettelli; Mario Caccamo; Mohamed Oukka; Howard L Weiner
Journal: Nature Date: 2008-03-23 Impact factor: 49.962

10. FICZ, a tryptophan photoproduct, suppresses pulmonary eosinophilia and Th2-type cytokine production in a mouse model of ovalbumin-induced allergic asthma.

Authors: Kyu-Tae Jeong; Sung-Jun Hwang; Gap-Soo Oh; Joo-Hung Park
Journal: Int Immunopharmacol Date: 2012-05-04 Impact factor: 4.932

10 in total

Platinum-catalyzed tandem indole annulation/arylation for the synthesis of diindolylmethanes and indolo[3,2-b]carbazoles.

Review 1. Isolation and synthesis of biologically active carbazole alkaloids.

2. Cationic ruthenium(II) catalysts for oxidative C-H/N-H bond functionalizations of anilines with removable directing group: synthesis of indoles in water.

Review 3. Progress in palladium-based catalytic systems for the sustainable synthesis of annulated heterocycles: a focus on indole backbones.

Review 4. Potential protective mechanisms of aryl hydrocarbon receptor (AHR) signaling in benign prostatic hyperplasia.

5. Recent advances in indole syntheses: new routes for a classic target.

6. Palladium(II)-catalyzed tandem cyclization/C-H functionalization of alkynes for the synthesis of functionalized indoles.

7. Synthesis of N-azolylindoles by copper-catalyzed C-H/N-H coupling-annulation sequence of o-alkynylanilines.

8. Exogenous stimuli maintain intraepithelial lymphocytes via aryl hydrocarbon receptor activation.

9. Control of T(reg) and T(H)17 cell differentiation by the aryl hydrocarbon receptor.

10. FICZ, a tryptophan photoproduct, suppresses pulmonary eosinophilia and Th2-type cytokine production in a mouse model of ovalbumin-induced allergic asthma.

1. Discovery of 2,3'-diindolylmethanes as a novel class of PCSK9 modulators.

2. Platinum-Catalyzed α,β-Unsaturated Carbene Formation in the Formal Syntheses of Frondosin B and Liphagal.

3. Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene.

4. Synthesis and biological evaluation of 2,3'-diindolylmethanes as agonists of aryl hydrocarbon receptor.

5. Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols.

6. Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles.

7. Synthesis and biological evaluation of FICZ analogues as agonists of aryl hydrocarbon receptor.

8. Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions.

9. Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor.

10. Synthesis of a Novel Type of 2,3'-BIMs via Platinum-Catalysed Reaction of Indolylallenes with Indoles.