Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization
Authors:
- 23 September 2016
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 18 (19) , 5170-5173
Abstract
A Ni-mediated cascade to a stereoselective synthesis of trans-tetrahydronaphtho[2,3-b]furans is efficiently achieved for the first time. The mild reductive system can be easily generated from inexpensive and air-stable materials and shows a broad positional tolerance of substituents that were previously difficult or impossible to access by other methods. Facile syntheses toward new analogues of therapeutic agents (iso)deoxypodophyllotoxin are also reported. In addition, the inherent substrate control is disclosed for the observed unique stereoselectivities during cyclizations.Keywords
Funding Information
- Ministry of Education of the People's Republic of China (lzujbky-2016-51, PCSIRT-15R28)
- National Natural Science Foundation of China (21472075)
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