The first total synthesis of (±)-furanether
A, which exhibits
good antifeedant activity, has been concisely achieved in 13 linear
steps. Notably, the key rigid tetracyclic skeleton containing a 1-methyl-8-oxabicyclo[3.2.1]octane
moiety with two vicinal quaternary carbon centers was rapidly constructed
in one step through a unique tandem C–H oxidation/oxa-[3,3]
Cope rearrangement/aldol cyclization sequence.
An efficient alkylcyanation of in situ generated arynes by N,N-disubstituted aminomalononitriles is described, enabling the direct synthesis of 2-substituted benzonitriles.
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