Ag(i)-catalyzed intramolecular transannulation of enynone tethered donor-acceptor cyclopropanes: a new synthesis of 2,3-dihydronaphtho[1,2-b]furansElectronic supplementary information (ESI) available: Experimental details, characterization of compounds, copies of 1H and 13C spectra for selected compounds, and CIF files of 3c, 3g and 3t. See DOI: 10.1039/c6cc07220h

An efficient AgOTf catalyzed tandem intramolecular transannulation of ((2-alkynyl)aryl)cyclopropyl ketones leading to the 2,3-dihydronaphtho[1,2- b ]furans has been developed. The reaction features a regioselective alkyne hydration, cyclopropylketone-2,3-dyhydrofuran rearrangement, and benzannulatio...

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Hauptverfasser: Dawande, Sudam Ganpat, Harode, Mandeep, Kalepu, Jagadeesh, Katukojvala, Sreenivas
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Sprache:eng
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Zusammenfassung:An efficient AgOTf catalyzed tandem intramolecular transannulation of ((2-alkynyl)aryl)cyclopropyl ketones leading to the 2,3-dihydronaphtho[1,2- b ]furans has been developed. The reaction features a regioselective alkyne hydration, cyclopropylketone-2,3-dyhydrofuran rearrangement, and benzannulation. The methodology gives direct access to the tricyclic core structure of biologically important 2,3-dihydronaphtho[1,2- b ]furan natural products. An efficient AgOTf catalyzed tandem intramolecular transannulation of ((2-alkynyl)aryl)cyclopropyl ketones leading to the 2,3-dihydronaphtho[1,2- b ]furans has been developed.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc07220h