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. 2024 Feb 2;26(4):775-780.
doi: 10.1021/acs.orglett.3c03782. Epub 2024 Jan 18.

Synthesis of the I-K Fused Polyether Array of CTX3C and Related Ciguatoxins by Use of a Gold-Catalyzed Cyclization Reaction

Venkaiah Chintalapudi  1 , Claire Wilson  1 , J Stephen Clark  1
Affiliations

Synthesis of the I-K Fused Polyether Array of CTX3C and Related Ciguatoxins by Use of a Gold-Catalyzed Cyclization Reaction

Venkaiah Chintalapudi et al. Org Lett. .

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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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Retrosynthetic analysis of CTX3C.
Scheme 1
Scheme 1. Gold-Catalyzed Formation of a Fused Seven-Membered Cyclic Ether
Scheme 2
Scheme 2. Synthesis of the IJ Fragment
Scheme 3
Scheme 3. Chain Extension for Ring K
Scheme 4
Scheme 4. Introduction of a K-Ring Methyl Substituent and Side Chain Functionalization
Scheme 5
Scheme 5. Synthesis of the L-Ring Fragment
Scheme 6
Scheme 6. Completion of the Fully Functionalized I–K Polyether Array of CTX3C
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