Synthetic Studies on Diazonamide A. Benzofuranone-Tyrosine and Indole-Oxazole Fragment Support Studies

Authors:
  • JKJoseph P. Konopelski
    Joseph P. Konopelski
  • JHJames M. Hottenroth
    James M. Hottenroth
  • HOHonorato Monzó Oltra
    Honorato Monzó Oltra
  • EVEduardo A. Véliz
    Eduardo A. Véliz
  • ZYZhi-Cai Yang
    Zhi-Cai Yang
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Abstract
This paper discloses efforts toward the total synthesis of the marine natural product cytotoxin diazonamide A. Specifically addressed are efficient procedures for the synthesis of suitably substituted benzofuranone and indole systems (C10-C17 and C18-C25 of the final product, respectively). In addition, methods for incorporation of the tyrosine residue, acylation of C10, elaboration of the C16-C18 biaryl bond, and formation of the oxazole ring comprising C26-C28 have been explored.