Beilstein J. Org. Chem.2020,16, 1320–1334, doi:10.3762/bjoc.16.113
- and pyrrolo-fused polycyclic indoles is herein described, starting from 2-formylpyrrole and employing Diels–Alder and Heck arylation reactions. 3-(N-Benzyl-2-pyrrolyl)acrylates and 4-(pyrrol-2-yl)butenones underwent a highly endo-Diels–Alder cycloaddition with maleimides to furnish octahydropyrrolo
in governing the endo stereocontrol.
Keywords: endo-Diels–Alder stereocontrol; 2-formylpyrrole; intramolecular Heck arylation reaction; non-covalent interactions; pyrroloindoles; pyrroloisoindoles; Introduction
Pyrrolizines [1][2] and pyrrolizidines [3][4], abundant in nature [4][5], are among the
route based on the functionalization of 2-formylpyrrole (13a), using recently described methodologies [41]. Firstly, 13a was reacted with the series of benzyl bromides 14a–d to produce adequately N-substituted five-membered aza-units 13b–e, respectively (Scheme 2), which were treated with the
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Graphical Abstract
Figure 1:
Fused aza-hetero polycyclic frames and natural pyrrolizine- and isoindole-containing alkaloids.