American Chemical Society
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Synthesis of the MN Ring of Caribbean Ciguatoxin C‑CTX‑1 via Desymmetrization by Acetal Formation

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journal contribution
posted on 2024-01-19, 20:31 authored by Masahiro Kaneko, Atsuhiro Yamashita, Yoko Yasuno, Kosei Yamauchi, Ken Sakai, Tohru Oishi
The MN ring of Caribbean ciguatoxin C-CTX-1 was synthesized from a meso-syn-2,7-dimethyloxepane derivative corresponding to the M ring via desymmetrization by acetal formation with a camphor derivative, followed by construction of the N ring via the Horner–Wadsworth–Emmons reaction and acetal formation. The meso-syn-2,7-dimethyloxepane derivative was synthesized via photoinduced electrocyclization of a conjugated exo-diene under flow conditions, giving a cyclobutene derivative, followed by ring expansion via oxidative cleavage and diastereoselective reduction of a β-hydroxy ketone.