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Synlett 2000; 2000(10): 1519-1521
DOI: 10.1055/s-2000-7641
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Self-Assembly of Amino Acid-Based Thiazoles and Oxazoles. Total Synthesis of Dendroamide A, a Cyclic Hexapeptide from the Cyanobacterium Stigonema dendroideum

Anna Bertram* , Gerald Pattenden
  • *School of Chemistry, The University of Nottingham, Nottingham, England NG7 2RD, UK; Fax + 44 (0) 115951 3564; E-mail: gp@nottingham.ac.uk
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Publication Date:
31 December 2000 (online)

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Treatment of a solution containing a 1 : 1 : 1 mixture of the chiral thiazole and oxazole-based amino acids 4, 8 and 9 with pentafluorodiphenylphosphinate in diisopropylethylamine in acetonitrile at room temperature for 2 h resulted in the formation of dendroamide A 7 (23%) and its positional isomer 15 (22%), together with symmetrical thiazole-based macrocyclic trimers in a combined yield of 30%. An independent, linear, synthesis of dendroamide A confirmed the structure and stereochemistry assigned to this natural cyclic hexapeptide.

self-assembly - cyclopeptides - dendroamide A