Synthesis and Structural Implication of the JKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1

Makoto Sasaki, Kotaro Iwasaki, Keisuke Arai

Research output: Contribution to journalArticlepeer-review

Abstract

Synthesis of the JKLMN-ring fragment of Caribbean ciguatoxin C-CTX-1, the causative toxin of ciguatera fish poisoning in the Caribbean Sea and the Northeast Atlantic areas, is described in detail. Key to the synthesis are a [2,3]-sigmatropic rearrangement to construct a seven-membered α-hydroxy exo-enol ether, stereoselective construction of an angular tetrasubstituted stereogenic center on the seven-membered M-ring by a hydrogen atom transfer-based reductive olefin coupling, Suzuki-Miyaura coupling of the KLMN-ring enol phosphate with a highly congested M-ring, and silica gel-mediated epoxide ring opening to form the J-ring. Comparison of the nuclear magnetic resonance spectroscopic data for the synthesized fragment with those for the natural product provided support for the formerly assigned structure of the N-ring in the right-hand terminal of C-CTX-1.

Original languageEnglish
Pages (from-to)4580-4597
Number of pages18
JournalJournal of Organic Chemistry
Volume86
Issue number6
DOIs
Publication statusPublished - 2021 Mar 19

ASJC Scopus subject areas

  • Organic Chemistry

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