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Issue 94, 2016
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Ag(i)-catalyzed intramolecular transannulation of enynone tethered donor–acceptor cyclopropanes: a new synthesis of 2,3-dihydronaphtho[1,2-b]furans

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Abstract

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.

Graphical abstract: Ag(i)-catalyzed intramolecular transannulation of enynone tethered donor–acceptor cyclopropanes: a new synthesis of 2,3-dihydronaphtho[1,2-b]furans

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Supplementary files

Article information


Submitted
04 Sep 2016
Accepted
01 Nov 2016
First published
07 Nov 2016

Chem. Commun., 2016,52, 13699-13701
Article type
Communication

Ag(I)-catalyzed intramolecular transannulation of enynone tethered donor–acceptor cyclopropanes: a new synthesis of 2,3-dihydronaphtho[1,2-b]furans

S. G. Dawande, M. Harode, J. Kalepu and S. Katukojvala, Chem. Commun., 2016, 52, 13699
DOI: 10.1039/C6CC07220H

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