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Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative agents of ciguatera food poisoning. The structure of CTX3C spans more than 3nm and is characterized by 13 ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the HIJKLM...
A stereoselective synthesis of the EFGH ring fragment of ciguatoxin CTX3C has been achieved through: (i) selective cleavage of a dioxepane acetal C O bond; (ii) radical cyclization to form the oxepane G ring; and (iii) chemoselective ring-closing metathesis of a triene yielding the hexahydrooxonin F ring.
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