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 Uenishi; James B. White; Masahiro Yonaga

doi:10.1021/ja00201a037

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

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

117 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(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.

Original language	English
Pages (from-to)	7525-7530
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	111
Issue number	19
DOIs	https://doi.org/10.1021/ja00201a037
Publication status	Published - 1989 Sept
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00201a037

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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

Armstrong, RW, Beau, JM, Cheon, SH, Christ, WJ, Fuiioka, 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. https://doi.org/10.1021/ja00201a037

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title = "Total Synthesis of a Fully Protected Palytoxin Carboxylic Acid",

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(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.",

author = "Armstrong, {Robert W.} and Beau, {Jean Marie} and Cheon, {Seung Hoon} and Christ, {William J.} and Hiromichi Fuiioka and Ham, {Won Hun} and Hawkins, {Lynn D.} and Haolun Jin and Kang, {Sung Ho} and Yoshito Kishi and Martinelli, {Michael J.} and McWhorter, {William W.} and Masanori Mizuno and Masaya Nakata and Stutz, {Arnold E.} and Talamas, {Francisco X.} and Mikio Taniguchi and Tino, {Joseph A.} and Katsuhiro Ueda and Uenishi, {Jun ichi} and White, {James B.} and Masahiro Yonaga",

year = "1989",

month = sep,

doi = "10.1021/ja00201a037",

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T1 - Total Synthesis of a Fully Protected Palytoxin Carboxylic Acid

AU - Armstrong, Robert W.

AU - Beau, Jean Marie

AU - Cheon, Seung Hoon

AU - Christ, William J.

AU - Fuiioka, 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

Y1 - 1989/9

N2 - 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.

AB - 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.

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ER -

Total Synthesis of a Fully Protected Palytoxin Carboxylic Acid

Abstract

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