A New Stereoselective Synthesis of Ciguatoxin Right Wing Fragments

Masayuki Inoue, Shuji Yamashita, Atsushi Tatami, Keisuke Miyazaki, Masahiro Hirama

Research output: Contribution to journalArticlepeer-review

49 Citations (Scopus)


The right wings (13 and 14) of ciguatoxins were synthesized highly stereoselectively. Key transformations in the synthesis are (i) an oxiranyl anion strategy to attach the H ring, (ii) intramolecular carbonyl olefination to cyclize the J ring, (iii) regio- and stereoselective reduction of the epoxyacetal to install the C42-stereocenter, and (iv) stereoselective reductive etherification to construct the K ring. The present procedure greatly improved the stereoselectivity and efficiency in comparison to a previous synthesis. Remarkably, only 23 steps were required from monocyclic I ring 5 to construct the ciguatoxin right wings. The high practicality of the present synthesis ensures a sufficient supply of these complex fragments for total syntheses and biomedical applications.

Original languageEnglish
Pages (from-to)2797-2804
Number of pages8
JournalJournal of Organic Chemistry
Issue number8
Publication statusPublished - 2004 Apr 16

ASJC Scopus subject areas

  • Organic Chemistry


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