Ag(i)-catalyzed intramolecular transannulation of enynone tethered donor-acceptor cyclopropanes: a new synthesis of 2,3-dihydronaphtho[1,2-b]furans.
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.
Department of Chemistry, Indian Institute of Science Education & Research, Bhopal, Madhya Pradesh 462066, India. sk@iiserb.ac.in.
Sudam Ganpat
SG
Dawande
Department of Chemistry, Indian Institute of Science Education & Research, Bhopal, Madhya Pradesh 462066, India. sk@iiserb.ac.in.
Mandeep
M
Harode
Department of Chemistry, Indian Institute of Science Education & Research, Bhopal, Madhya Pradesh 462066, India. sk@iiserb.ac.in.
Jagadeesh
J
Kalepu
Department of Chemistry, Indian Institute of Science Education & Research, Bhopal, Madhya Pradesh 462066, India. sk@iiserb.ac.in.
Sreenivas
http://orcid.org/0000-0001-8232-6431
S
Katukojvala