Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

Shoji Kobayashi, Yusuke Takahashi, Kazuo Komano, Babak H. Alizadeh, Yuuya Kawada, Tohru Oishi, Shin Ichiro Tanaka, Yoshihiro Ogasawara, Shin Ya Sasaki, Masahiro Hirama

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. Graphical Abstract.

Original languageEnglish
Pages (from-to)8375-8396
Number of pages22
JournalTetrahedron
Volume60
Issue number38
DOIs
Publication statusPublished - Sep 13 2004
Externally publishedYes

Fingerprint

Ciguatoxins
Ciguatera Poisoning
Alkylation
Condensation
3-hydroxybutanal
ciguatoxin 3C

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Kobayashi, S., Takahashi, Y., Komano, K., Alizadeh, B. H., Kawada, Y., Oishi, T., ... Hirama, M. (2004). Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C. Tetrahedron, 60(38), 8375-8396. https://doi.org/10.1016/j.tet.2004.07.010

Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C. / Kobayashi, Shoji; Takahashi, Yusuke; Komano, Kazuo; Alizadeh, Babak H.; Kawada, Yuuya; Oishi, Tohru; Tanaka, Shin Ichiro; Ogasawara, Yoshihiro; Sasaki, Shin Ya; Hirama, Masahiro.

In: Tetrahedron, Vol. 60, No. 38, 13.09.2004, p. 8375-8396.

Research output: Contribution to journalArticle

Kobayashi, S, Takahashi, Y, Komano, K, Alizadeh, BH, Kawada, Y, Oishi, T, Tanaka, SI, Ogasawara, Y, Sasaki, SY & Hirama, M 2004, 'Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C', Tetrahedron, vol. 60, no. 38, pp. 8375-8396. https://doi.org/10.1016/j.tet.2004.07.010
Kobayashi S, Takahashi Y, Komano K, Alizadeh BH, Kawada Y, Oishi T et al. Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C. Tetrahedron. 2004 Sep 13;60(38):8375-8396. https://doi.org/10.1016/j.tet.2004.07.010
Kobayashi, Shoji ; Takahashi, Yusuke ; Komano, Kazuo ; Alizadeh, Babak H. ; Kawada, Yuuya ; Oishi, Tohru ; Tanaka, Shin Ichiro ; Ogasawara, Yoshihiro ; Sasaki, Shin Ya ; Hirama, Masahiro. / Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C. In: Tetrahedron. 2004 ; Vol. 60, No. 38. pp. 8375-8396.
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