posted on 2024-01-19, 03:03authored byVenkaiah Chintalapudi, Claire Wilson, J. Stephen Clark
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.