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Literature DB >> 21857755

Preparation of phenalenes and hydronaphthacenes through tandem alkyne Fischer-carbene complex coupling and inter- or intramolecular Diels-Alder reactions.

Rajesh Kumar Patti¹, Shaofeng Duan, Zhipeng Wang, James W Herndon.

Abstract

The rapid construction of phenalenes through the reaction of 8-alkynyltetralones with Fischer carbine complexes followed by either inter- or an intramolecular Diels-Alder reaction is presented. As a showcase of the synthetic utility of this process, the rapid construction of polycyclic ring systems containing the tetracycline core has been demonstrated through an iterative application of this reaction sequence.

Entities: Chemical Disease Gene

Year: 2011 PMID： 21857755 PMCID： PMC3156453 DOI： 10.1016/j.tetlet.2011.06.006

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

19 in total

1. Benzopyrenomycin, a cytotoxic bacterial polyketide metabolite with a benzo[a]pyrene-type carbocyclic ring system.

Authors: Xueshi Huang; Jian He; Xuemei Niu; Klaus-Dieter Menzel; Hans-Martin Dahse; Susanne Grabley; Hans-Peter Fiedler; Isabel Sattler; Christian Hertweck
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Synthesis of 1-aryl-1H-indazoles via palladium-catalyzed intramolecular amination of aryl halides.

Authors: Artyom Y Lebedev; Anton S Khartulyari; Alexander Z Voskoboynikov
Journal: J Org Chem Date: 2005-01-21 Impact factor: 4.354

3. Synthesis of ¹³C₂-Benzo[a]pyrene and its 7,8-Dihydrodiol and 7,8-Dione Implicated as Carcinogenic Metabolites.

Authors: Chongzhao Ran; Daiwang Xu; Qing Dai; Trevor M Penning; Ian A Blair; Ronald G Harvey
Journal: Tetrahedron Lett Date: 2008-07-21 Impact factor: 2.415

4. Generation and trapping of isobenzofuran intermediates formed in the coupling of Fischer carbene complexes and o-alkynylbenzoyl derivatives

Authors:
Journal: Org Lett Date: 2000-05-04 Impact factor: 6.005

5. Synthesis of (1S,3aS)-8-(2,3,3a,4,5, 6-hexahydro-1H-phenalen-1-yl)-1-phenyl-1,3,8-triaza-spiro[4. 5]decan-4-one, a potent and selective orphanin FQ (OFQ) receptor agonist with anxiolytic-like properties.

Authors: J Wichmann; G Adam; S Röver; M Hennig; M Scalone; A M Cesura; F M Dautzenberg; F Jenck
Journal: Eur J Med Chem Date: 2000-09 Impact factor: 6.514

6. Electronic Control of Product Distribution in the [5+5]-Coupling of ortho-Alkynylbenzaldehyde Derivatives and γ,δ-Unsaturated Carbene Complexes.

Authors: Alejandro Camacho-Davila; Lalith S R Gamage; Zhipeng Wang; James W Herndon
Journal: Tetrahedron Date: 2010-07 Impact factor: 2.457

7. Synthesis of alkylidenephthalans through fluoride-induced cyclization of electron-deficient 2-siloxymethylphenylacetylene derivatives.

Authors: Shaofeng Duan; Karen Cress; Kris Waynant; Elias Ramos-Miranda; James W Herndon
Journal: Tetrahedron Date: 2007-04-02 Impact factor: 2.457

8. Synthesis of naphthalenes through three-component coupling of alkynes, Fischer carbene complexes, and benzaldehyde hydrazones via isoindole intermediates.

Authors: Shaofeng Duan; Dilip K Sinha-Mahapatra; James W Herndon
Journal: Org Lett Date: 2008-03-20 Impact factor: 6.005

Preparation of phenalenes and hydronaphthacenes through tandem alkyne Fischer-carbene complex coupling and inter- or intramolecular Diels-Alder reactions.

1. Benzopyrenomycin, a cytotoxic bacterial polyketide metabolite with a benzo[a]pyrene-type carbocyclic ring system.

2. Synthesis of 1-aryl-1H-indazoles via palladium-catalyzed intramolecular amination of aryl halides.

3. Synthesis of ¹³C₂-Benzo[a]pyrene and its 7,8-Dihydrodiol and 7,8-Dione Implicated as Carcinogenic Metabolites.

4. Generation and trapping of isobenzofuran intermediates formed in the coupling of Fischer carbene complexes and o-alkynylbenzoyl derivatives

5. Synthesis of (1S,3aS)-8-(2,3,3a,4,5, 6-hexahydro-1H-phenalen-1-yl)-1-phenyl-1,3,8-triaza-spiro[4. 5]decan-4-one, a potent and selective orphanin FQ (OFQ) receptor agonist with anxiolytic-like properties.

6. Electronic Control of Product Distribution in the [5+5]-Coupling of ortho-Alkynylbenzaldehyde Derivatives and γ,δ-Unsaturated Carbene Complexes.

7. Synthesis of alkylidenephthalans through fluoride-induced cyclization of electron-deficient 2-siloxymethylphenylacetylene derivatives.

8. Synthesis of naphthalenes through three-component coupling of alkynes, Fischer carbene complexes, and benzaldehyde hydrazones via isoindole intermediates.

9. Regiospecific metalation of oligobromobenzenes.

Review 10. Phospholipase A2 inhibitors from marine organisms.

1. Total synthesis of (+)-antofine and (-)-cryptopleurine.

2. The [5+5] route to the phenanthrene skeleton.