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Intramolecular Cyclization Strategies Toward the Synthesis of Zoanthamine Alkaloids.

ABSTRACT: Stabilized 2-amino-1,3-dienes can participate in intramolecular Diels-Alder (IMDA) reactions with pendant dienophiles. We found that these dienes can be readily prepared via standard palladium-mediated coupling reactions and have comparable reactivity to 2-oxodienes. Application of these substrates to the synthesis of tetracyclic model systems representing the ABCE motif of the zoanthamines is presented.

SUBMITTER: Fischer D

PROVIDER: S-EPMC3157960 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Intramolecular Cyclization Strategies Toward the Synthesis of Zoanthamine Alkaloids.

Fischer Derek D Nguyen Thong X TX Trzoss Lynnie L Dakanali Marianna M Theodorakis Emmanuel A EA

Tetrahedron letters 20110901 38

Stabilized 2-amino-1,3-dienes can participate in intramolecular Diels-Alder (IMDA) reactions with pendant dienophiles. We found that these dienes can be readily prepared via standard palladium-mediated coupling reactions and have comparable reactivity to 2-oxodienes. Application of these substrates to the synthesis of tetracyclic model systems representing the ABCE motif of the zoanthamines is presented. ...[more]

PMID: 21857757

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