Stereoselective synthesis of a potential intermediate bearing 11-oxabicyclo[6.2.1]undec-3-ene core, a common scaffold of biologically active germacrane-type sesquiterpenes, has been achieved. Synthetic features involve formal 1,3-asymmetric induction, unusual ring-closing metathesis constructing a 10-membered carbocycle system, and unique lactone transposition.
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