Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids

• Published in: Tetrahedron letters Vol. 52; no. 38; pp. 4920 - 4923
• Main Authors: Fischer, Derek, Nguyen, Thong X., Trzoss, Lynnie, Dakanali, Marianna, Theodorakis, Emmanuel A.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 21.09.2011; Elsevier
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Alkaloids; Aminodiene; Chemical reactions; chemical structure; Chemistry; Chemistry, Organic; Cycloaddition; Diels–Alder reaction; Dienes; Exact sciences and technology; Jewelry; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stille coupling; Strategy; Synthesis (chemistry); Tetrahedrons; Zoanthamine; Stille coupling; Cycloaddition; Zoanthamine; Diels–Alder reaction; Aminodiene; RING MOTIF; DIELS-ALDER REACTIONS; ENANTIOSELECTIVE SYNTHESIS; MARINE ZOANTHID; CROSS-CONJUGATED AZATRIENES; Diels-Alder reaction; NORZOANTHAMINE; CIS/TRANS-SELECTIVITY; DERIVATIVES; ESTER-LINKED 1,3,9-DECATRIENES; Intramolecular reaction; Alkaloid; Cyclization; Diels Alder addition; Chemical synthesis
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.07.054

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.