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Synlett 1996; 1996(7): 609-611
DOI: 10.1055/s-1996-5566
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Synthetic Studies on Diazonamide A. Benzofuranone-Tyrosine and Indole-Oxazole Fragment Support Studies

Joseph P. Konopelski* , James M. Hottenroth, Honorato Monzó Oltra, Eduardo A. Véliz, Zhi-Cai Yang
  • *Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA 95064, USA, FAX 408-459-2935; joek@chemistry.ucsc.edu
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Publication Date:
31 December 2000 (online)

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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.

arylation - organolead - acylation - indoles - oxazoles