Convergent synthesis of the EFGH ring fragment of ciguatoxin CTX3C

Hiroto Imai, Hisatoshi Uehara, Masayuki Inoue, Hiroki Oguri, Tohru Oishi, Masahiro Hirama

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

A stereoselective synthesis of the EFGH ring fragment of ciguatoxin CTX3C has been achieved through: (i) selective cleavage of a dioxepane acetal C-O bond; (ii) radical cyclization to form the oxepane G ring; and (iii) chemoselective ring-closing metathesis of a triene yielding the hexahydrooxonin F ring.

Original languageEnglish
Pages (from-to)6219-6222
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number35
DOIs
Publication statusPublished - Aug 27 2001
Externally publishedYes

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Acetals
Cyclization
ciguatoxin 3C

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Convergent synthesis of the EFGH ring fragment of ciguatoxin CTX3C. / Imai, Hiroto; Uehara, Hisatoshi; Inoue, Masayuki; Oguri, Hiroki; Oishi, Tohru; Hirama, Masahiro.

In: Tetrahedron Letters, Vol. 42, No. 35, 27.08.2001, p. 6219-6222.

Research output: Contribution to journalArticle

Imai, H, Uehara, H, Inoue, M, Oguri, H, Oishi, T & Hirama, M 2001, 'Convergent synthesis of the EFGH ring fragment of ciguatoxin CTX3C', Tetrahedron Letters, vol. 42, no. 35, pp. 6219-6222. https://doi.org/10.1016/S0040-4039(01)01219-9
Imai, Hiroto ; Uehara, Hisatoshi ; Inoue, Masayuki ; Oguri, Hiroki ; Oishi, Tohru ; Hirama, Masahiro. / Convergent synthesis of the EFGH ring fragment of ciguatoxin CTX3C. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 35. pp. 6219-6222.
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