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

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.

SUBMITTER: Patti RK

PROVIDER: S-EPMC3156453 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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

Patti Rajesh Kumar RK Duan Shaofeng S Wang Zhipeng Z Herndon James W JW

Tetrahedron letters 20110801 32

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. ...[more]

PMID: 21857755

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