Total Synthesis of Palytoxin Carboxylic Acid and Palytoxin Amide

Robert W. Armstrong, Jean Marie Beau, Seung Hoon Cheon, William J. Christ, Hiromichi Fujioka, Won Hun Ham, Lynn D. Hawkins, Haolun Jin, Sung Ho Kang, Yoshito Kishi, Michael J. Martinelli, William W. McWhorter, Masanori Mizuno, Masaya Nakata, Arnold E. Stutz, Francisco X. Talamas, Mikio Taniguchi, Joseph A. Tino, Katsuhiro Ueda, Jun ichi UenishiJames B. White, Masahiro Yonaga

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104 Citations (Scopus)

Abstract

The total synthesis of palytoxin carboxylic acid and palytoxin amide was achieved from the fully protected palytoxin carboxylic acid. The fully protected palytoxin carboxylic acid 1 contains eight different and 42 total protecting groups. All these protecting groups were successfully removed in five synthetic operations, i.e., (1) DDQ treatment, (2) aqueous HClO4 hydrolysis, (3) aqueous LiOH hydrolysis, (4) (n-Bu)4NF treatment, and (5) aqueous AcOH hydrolysis. The completely deprotected palytoxin carboxylic acid was isolated in approximately 35% overall yield and identified with the authentic sample. An efficient method to convert palytoxin carboxylic acid 2 into palytoxin amide 3 was developed.

Original languageEnglish
Pages (from-to)7530-7533
Number of pages4
JournalJournal of the American Chemical Society
Volume111
Issue number19
DOIs
Publication statusPublished - 1989 Sep

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Armstrong, R. W., Beau, J. M., Cheon, S. H., Christ, W. J., Fujioka, H., Ham, W. H., Hawkins, L. D., Jin, H., Kang, S. H., Kishi, Y., Martinelli, M. J., McWhorter, W. W., Mizuno, M., Nakata, M., Stutz, A. E., Talamas, F. X., Taniguchi, M., Tino, J. A., Ueda, K., ... Yonaga, M. (1989). Total Synthesis of Palytoxin Carboxylic Acid and Palytoxin Amide. Journal of the American Chemical Society, 111(19), 7530-7533. https://doi.org/10.1021/ja00201a038