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Diastereoselective Synthesis of Tetracyclic Indoles via Stepwise Annulative Skeletal Editing of Azofurans
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DOI：10.1002/adsc.70589.png)
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Abstract
En 中文
Stepwise annulative skeletal editing of azofurans with 2-vinylindoles is reported, enabling a Brønsted acid-catalyzed dearomative skeletal rearrangement of azofurans and an electrophilic halogen reagent (NXS)-mediated aminohalogenation cascade to produce 32 examples of tetracyclic indoles in good yields with excellent diastereoselectivity (>19:1 dr in all cases). Remarkably, an extended one-pot three-step sequence, which incorporated an additional hydrogen bromide elimination step into the above transformations, afforded tetracyclic indoles bearing an exocyclic terminal alkene motif. This protocol demonstrates a broad substrate scope and good functional-group tolerance, enabling the transformation of planar 2D aromatic furans into 3D tetracyclic indoles with complete regio- and diastereoselectivities.
Keywords:
annulative skeletal editing
azofurans
dearomatization
diastereoselectivity
tetracyclic indoles
Journal
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4
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