A wide array of aldehydes undergo smooth cross‐coupling with 5,6‐bis(2‐hydroxyethyl)‐2‐phenyl‐3a,4,7,7a‐tetrahydro‐1H‐isoindole‐1,3(2H)‐dione in the presence of 1.2 equiv. TMSOTf at –78 °C in dichloromethane to afford the corresponding hexahydro‐8a,4a‐(epoxyethano)pyrano[3,4‐f]isoindole‐1,3(2H,5H)‐dione derivatives in good yields with excellent diastereoselectivity. This is the first report on the stereoselective construction of oxa‐bridged tetracyclic frameworks through a bicyclization strategy.
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