The GHIJKL fragment
of gymnocin-B was synthesized using the oxiranyl anion strategy. The
first highlight of the synthesis is the bromoketone cyclization reaction
on the oxepane ring to construct the fused bisoxepane GH ring. The
second key step is the introduction of the trans-4-hydroxy-3-methyloxepane
J ring via addition of trimethylaluminum to a conjugated oxonium moiety,
followed by diastereoselective epoxidation and regioselective reduction.
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