Synthesis of the I–K Fused Polyether Array of CTX3C and Related Ciguatoxins by Use of a Gold-Catalyzed Cyclization Reaction
Venkaiah Chintalapudi, Claire Wilson, J. Stephen Clark
TL;DR
Scientists synthesized a complex part of the CTX3C toxin using a gold-catalyzed reaction, making it easier to study and understand.
Contribution
A new gold-catalyzed cyclization method was developed for synthesizing a key part of ciguatoxins.
Findings
The I–K fragment of CTX3C was synthesized from a chiral pool-derived alcohol.
A gold-catalyzed cyclization efficiently formed ring K under mild conditions.
The tricyclic fragment with a dimethyl-substituted side chain was successfully created.
Abstract
The I–K fragment (C31–C49) of the ciguatoxin CTX3C has been synthesized from a simple chiral pool derived tetrahydropyranyl alcohol. An efficient gold-catalyzed cyclization reaction of a γ′-hydroxy ynone has been used to accomplish efficient closure of ring K under mild conditions. The resulting vinylogous ester has been elaborated to give a complete tricyclic fragment bearing the dimethyl-substituted side chain required for assembly of the LM spirocyclic acetal portion of the target.
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Taxonomy
TopicsMarine Toxins and Detection Methods · Oxidative Organic Chemistry Reactions · Chemical synthesis and alkaloids