Total synthesis of a fully protected palytoxin carboxylic acid

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

107 Citations (Scopus)

Abstract

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(II)/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/EuCl3 reduction.

Original languageEnglish
Pages (from-to)7525-7530
Number of pages6
JournalJournal of the American Chemical Society
Volume111
Issue number19
Publication statusPublished - 1989
Externally publishedYes

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Hydrogenation
Carboxylic Acids
Carboxylic acids
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 a fully protected palytoxin carboxylic acid. Journal of the American Chemical Society, 111(19), 7525-7530.

Total synthesis of a fully protected palytoxin carboxylic acid. / 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. 7525-7530.

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 a fully protected palytoxin carboxylic acid', Journal of the American Chemical Society, vol. 111, no. 19, pp. 7525-7530.
Armstrong RW, Beau JM, Cheon SH, Christ WJ, Fujioka H, Ham WH et al. Total synthesis of a fully protected palytoxin carboxylic acid. Journal of the American Chemical Society. 1989;111(19):7525-7530.
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 a fully protected palytoxin carboxylic acid. In: Journal of the American Chemical Society. 1989 ; Vol. 111, No. 19. pp. 7525-7530.
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AU - Ham, Won Hun

AU - Hawkins, Lynn D.

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AU - Kang, Sung Ho

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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

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