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

研究成果: Article査読

109 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)7530-7533
ページ数4
ジャーナルJournal of the American Chemical Society
111
19
DOI
出版ステータスPublished - 1989 9
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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