Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids

Derek Fischer, Thong X. Nguyen, Lynnie Trzoss, Marianna Dakanali, Emmanuel A. Theodorakis

Research output: Contribution to journalArticle

9 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)4920-4923
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number38
DOIs
StatePublished - Sep 21 2011

Fingerprint

Cyclization
Cycloaddition Reaction
Palladium
Alkaloids
Substrates
zoanthamine

Keywords

  • Aminodiene
  • Cycloaddition
  • Diels-Alder reaction
  • Stille coupling
  • Zoanthamine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids. / Fischer, Derek; Nguyen, Thong X.; Trzoss, Lynnie; Dakanali, Marianna; Theodorakis, Emmanuel A.

In: Tetrahedron Letters, Vol. 52, No. 38, 21.09.2011, p. 4920-4923.

Research output: Contribution to journalArticle

Fischer, Derek ; Nguyen, Thong X. ; Trzoss, Lynnie ; Dakanali, Marianna ; Theodorakis, Emmanuel A. / Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids. In: Tetrahedron Letters. 2011 ; Vol. 52, No. 38. pp. 4920-4923.
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