The intramolecular Diels-Alder vinylfuran (IMDAV) reaction: a short approach to aza-analogues of pinguisane-type sesquiterpenes

摘要

The reaction of readily accessible (3-furyl)allylamines with maleic anhydride, followed by a domino sequence involving acylation/cycloaddition/proton shift steps, led to the formation of furo[2,3-f]-isoindoles-the aza-analogs of pinguisane-type sesquiterpenes. The key intramolecular Diels-Alder vinylfuran (IMDAV) reaction proceeded under mild conditions, with high levels of diastereoselectivity and satisfactory yields. (C) 2015 Elsevier Ltd. All rights reserved.