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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]

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