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

46 Citations (Scopus)

Abstract

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
Volume69
Issue number8
DOIs
Publication statusPublished - 2004 Apr 16

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'A New Stereoselective Synthesis of Ciguatoxin Right Wing Fragments'. Together they form a unique fingerprint.

Cite this