Synthesis of the I-K fused polyether array of CTX3C and related ciguatoxins by use of a gold-catalyzed cyclization reaction

Chintalapudi, V., Wilson, C. and Clark, J. S. (2024) Synthesis of the I-K fused polyether array of CTX3C and related ciguatoxins by use of a gold-catalyzed cyclization reaction. Organic Letters, 26(4), pp. 769-976. (doi: 10.1021/acs.orglett.3c03782) (PMID:38238251) (PMCID:PMC10845158)

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.

• Item Type: Articles
• Additional Information: This work was supported by funding from EPSRC (Grant no. EP/R035423/1).
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Clark, Professor Stephen and Wilson, Dr Claire and Chintalapudi, Dr Rer Nat Venkaiah
• Authors: Chintalapudi, V., Wilson, C., and Clark, J. S.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic Letters
• Publisher: American Chemical Society
• ISSN: 1523-7060
• ISSN (Online): 1523-7052
• Published Online: 18 January 2024
• Copyright Holders: Copyright © 2024 The Authors
• First Published: First published in Organic Letters 26(4):775-780
• Publisher Policy: Reproduced under a Creative Commons licence

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
302433		Convergent Bidirectional Total Synthesis of Ciguatoxin CTX3C	Stephen Clark	Engineering and Physical Sciences Research Council (EPSRC)	EP/R035423/1	Chemistry