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 Uenishi; James B. White; Masahiro Yonaga

doi:10.1021/ja00201a038

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 journal › Article › peer-review

117 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 language	English
Pages (from-to)	7530-7533
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	111
Issue number	19
DOIs	https://doi.org/10.1021/ja00201a038
Publication status	Published - 1989 Sep
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00201a038

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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

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, 09.1989, p. 7530-7533.

Research output: Contribution to journal › Article › peer-review

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. https://doi.org/10.1021/ja00201a038

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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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.",

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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 - 1989/9

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AB - 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.

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Total Synthesis of Palytoxin Carboxylic Acid and Palytoxin Amide

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