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 language | English |
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Pages (from-to) | 2797-2804 |
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Volume | 69 |
Issue number | 8 |
DOIs | |
Publication status | Published - 2004 Apr 16 |
ASJC Scopus subject areas
- Organic Chemistry