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Literature DB >> 23574045

Metal-catalyzed cascade rearrangements of 3-alkynyl flavone ethers.

Yuan Xiong¹, Scott E Schaus, John A Porco.

Abstract

Metal-mediated rearrangements of 3-alkynyl flavone ethers are reported. The overall process involves 5-endo enyne cyclization to a platinum-containing spiro-oxocarbenium intermediate which may be trapped with methanol to produce spirodihydrofurans or further rearranged to afford either allenyl chromanediones or benzofuranones.

Entities: Chemical Disease Gene

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Year: 2013 PMID： 23574045 PMCID： PMC3773515 DOI： 10.1021/ol400631b

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

37 in total

1. Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective Saucy-Marbet Claisen rearrangement.

Authors: Trung Cao; Joshua Deitch; Elizabeth C Linton; Marisa C Kozlowski
Journal: Angew Chem Int Ed Engl Date: 2012-01-27 Impact factor: 15.336

2. The mechanistic puzzle of transition-metal-catalyzed skeletal rearrangements of enynes.

Authors: Cristina Nieto-Oberhuber; Salomé López; Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal: Chemistry Date: 2006-08-07 Impact factor: 5.236

Review 3. Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective.

Authors: Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal: Chem Rev Date: 2008-07-18 Impact factor: 60.622

4. Rhodium-catalyzed cascade reactions of dienynes leading to substituted dihydronaphthalenes and naphthalenes.

Authors: Eri Okazaki; Ryuichi Okamoto; Yu Shibata; Keiichi Noguchi; Ken Tanaka
Journal: Angew Chem Int Ed Engl Date: 2012-05-24 Impact factor: 15.336

5. Synthesis of stable 2H-pyran-5-carboxylates via a catalyzed propargyl-Claisen rearrangement/oxa-6pi electrocyclization strategy.

Authors: Helge Menz; Stefan F Kirsch
Journal: Org Lett Date: 2006-10-12 Impact factor: 6.005

Metal-catalyzed cascade rearrangements of 3-alkynyl flavone ethers.

1. Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective Saucy-Marbet Claisen rearrangement.

2. The mechanistic puzzle of transition-metal-catalyzed skeletal rearrangements of enynes.

Review 3. Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective.

4. Rhodium-catalyzed cascade reactions of dienynes leading to substituted dihydronaphthalenes and naphthalenes.

5. Synthesis of stable 2H-pyran-5-carboxylates via a catalyzed propargyl-Claisen rearrangement/oxa-6pi electrocyclization strategy.

6. Gold-catalyzed assembly of heterobicyclic systems.

7. Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

8. Mechanistic studies on Au(I)-catalyzed [3,3]-sigmatropic rearrangements using cyclopropane probes.

9. Au-catalyzed tandem cyclization/[1,2]-alkyl migration reaction of epoxy alkynes: synthesis of spiropyranones.

10. Pt(IV)-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation.

1. Combinatorial Synthesis of Structurally Diverse Triazole-Bridged Flavonoid Dimers and Trimers.