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

Research output: Contribution to journalArticle

103 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
Publication statusPublished - 1989
Externally publishedYes

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Carboxylic Acids
Carboxylic acids
Amides
Hydrolysis
palytoxin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Armstrong, R. W., Beau, J. M., Cheon, S. H., Christ, W. J., Fujioka, H., Ham, W. H., ... Yonaga, M. (1989). Total synthesis of palytoxin carboxylic acid and palytoxin amide. Journal of the American Chemical Society, 111(19), 7530-7533.

Total synthesis of palytoxin carboxylic acid and palytoxin amide. / Armstrong, Robert W.; Beau, Jean Marie; Cheon, Seung Hoon; Christ, William J.; Fujioka, Hiromichi; Ham, Won Hun; Hawkins, Lynn D.; Jin, Haolun; Kang, Sung Ho; Kishi, Yoshito; Martinelli, Michael J.; McWhorter, William W.; Mizuno, Masanori; Nakata, Masaya; Stutz, Arnold E.; Talamas, Francisco X.; Taniguchi, Mikio; Tino, Joseph A.; Ueda, Katsuhiro; Uenishi, Jun Ichi; White, James B.; Yonaga, Masahiro.

In: Journal of the American Chemical Society, Vol. 111, No. 19, 1989, p. 7530-7533.

Research output: Contribution to journalArticle

Armstrong, RW, Beau, JM, Cheon, SH, Christ, WJ, Fujioka, H, Ham, WH, Hawkins, LD, Jin, H, Kang, SH, Kishi, Y, Martinelli, MJ, McWhorter, WW, Mizuno, M, Nakata, M, Stutz, AE, Talamas, FX, Taniguchi, M, Tino, JA, Ueda, K, Uenishi, JI, White, JB & Yonaga, M 1989, 'Total synthesis of palytoxin carboxylic acid and palytoxin amide', Journal of the American Chemical Society, vol. 111, no. 19, pp. 7530-7533.
Armstrong RW, Beau JM, Cheon SH, Christ WJ, Fujioka H, Ham WH et al. Total synthesis of palytoxin carboxylic acid and palytoxin amide. Journal of the American Chemical Society. 1989;111(19):7530-7533.
Armstrong, Robert W. ; Beau, Jean Marie ; Cheon, Seung Hoon ; Christ, William J. ; Fujioka, Hiromichi ; Ham, Won Hun ; Hawkins, Lynn D. ; Jin, Haolun ; Kang, Sung Ho ; Kishi, Yoshito ; Martinelli, Michael J. ; McWhorter, William W. ; Mizuno, Masanori ; Nakata, Masaya ; Stutz, Arnold E. ; Talamas, Francisco X. ; Taniguchi, Mikio ; Tino, Joseph A. ; Ueda, Katsuhiro ; Uenishi, Jun Ichi ; White, James B. ; Yonaga, Masahiro. / Total synthesis of palytoxin carboxylic acid and palytoxin amide. In: Journal of the American Chemical Society. 1989 ; Vol. 111, No. 19. pp. 7530-7533.
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AU - Beau, Jean Marie

AU - Cheon, Seung Hoon

AU - Christ, William J.

AU - Fujioka, Hiromichi

AU - Ham, Won Hun

AU - Hawkins, Lynn D.

AU - Jin, Haolun

AU - Kang, Sung Ho

AU - Kishi, Yoshito

AU - Martinelli, Michael J.

AU - McWhorter, William W.

AU - Mizuno, Masanori

AU - Nakata, Masaya

AU - Stutz, Arnold E.

AU - Talamas, Francisco X.

AU - Taniguchi, Mikio

AU - Tino, Joseph A.

AU - Ueda, Katsuhiro

AU - Uenishi, Jun Ichi

AU - White, James B.

AU - Yonaga, Masahiro

PY - 1989

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