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

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
巻	111
号	19
DOI	https://doi.org/10.1021/ja00201a038
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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10.1021/ja00201a038

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引用スタイル

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.

研究成果: Article › 査読

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 - Stutz, Arnold E.

AU - Talamas, Francisco X.

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AU - Tino, Joseph A.

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Total Synthesis of Palytoxin Carboxylic Acid and Palytoxin Amide

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