1 research outputs found
Synthesis of the MN Ring of Caribbean Ciguatoxin C‑CTX‑1 via Desymmetrization by Acetal Formation
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