A Zn(OTf)-catalyzed (4+4) cyclocondensation of anthranils with 2-(-1-aroyl-2-arylcyclopropyl)malonates delivers a range of polycyclic benzazocines featuring an oxa-bridged eight-membered ring in excellent yields and with exclusive diastereoselectivity. Further synthetic manipulations of these products enable rapid access to diverse useful heterocyclic molecular scaffolds.
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