Total Synthesis of a Fully Protected Palytoxin Carboxylic Acid

Robert W. Armstrong, Jean Marie Beau, Seung Hoon Cheon, William J. Christ, Hiromichi Fuiioka, 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

107 引用 (Scopus)

抜粋

The total synthesis of a fully protected palytoxin carboxylic acid was achieved from eight building blocks 1, 2, 4, 6, 8, 9, 11, and 13. The C.22-C.23 and C.37-C.38 bonds were formed via Wittig olefination, followed by hydrogenation. The Ni(lI)/Cr(II)-mediated coupling reaction was utilized for formation of the C.7-C.8 and C.84-C.85 bonds. The TlOH-accelerated diene synthesis was applied for formation of the C.75-C.76 bond. The C.98-C.99 olefinic bond was introduced by a Wittig reaction, whereas the C.51-C.52 olefinic bond was introduced by a Horner-Emmons reaction, followed by stereoselective LiBH4/EuCl3reduction.

元の言語English
ページ(範囲)7525-7530
ページ数6
ジャーナルJournal of the American Chemical Society
111
発行部数19
DOI
出版物ステータスPublished - 1989 9

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., Fuiioka, 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 a Fully Protected Palytoxin Carboxylic Acid. Journal of the American Chemical Society, 111(19), 7525-7530. https://doi.org/10.1021/ja00201a037