Stereoselective Synthesis of the I–L Fragment of the Pacific Ciguatoxins
Open Access
- 24 November 2020
- Vol. 12 (12), 740
- https://doi.org/10.3390/toxins12120740
Abstract
The I–L ring system found in all the Pacific ciguatoxins has been prepared from a tricyclic precursor in a highly stereoselective manner. Subtle differences in the reactivity of the enones present in the seven- and eight-membered rings of the tricyclic ether starting material have been exploited to allow selective protection of the enone in the eight-membered ring. Subsequent distereoselective allylation of the seven-membered ring has been accomplished by a palladium-mediated Tsuji-Trost reaction. The K-ring methyl and hydroxyl groups have been installed in a highly stereoselective manner by sequential conjugate reduction and enolate oxidation reactions. Ring L has been constructed by a use of a novel relay ring-closing metathesis reaction to complete the tetracyclic framework, which possesses the functionality necessary for elaboration of rings I and L and the introduction of ring M.Keywords
Funding Information
- UK Research and Innovation (EP/K503058 and EP/L50497X)
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