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Stereoselective Synthesis of Oxa- and Aza-Angular Triquinanes Using Tandem Radical Cyclization to Vinylogous Carbonates and Carbamates

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Title Stereoselective Synthesis of Oxa- and Aza-Angular Triquinanes Using Tandem Radical Cyclization to Vinylogous Carbonates and Carbamates
 
Creator GHARPURE, SJ
NIRANJANA, P
PORWAL, SK
 
Subject CLOSING METATHESIS APPROACH
BAYLIS-HILLMAN REACTION
ILLICIUM-MERRILLIANUM
ORGANIC-SYNTHESIS
MICHAEL ADDITION
NATURAL-PRODUCTS
CYCLIC ETHERS
CONSTRUCTION
CYCLOADDITION
DIOXATRIQUINANES
 
Description Tandem radical cyclization to vinylogous carbonates and carbamates is developed for a new, highly stereoselective synthesis of heterocyclic angular triquinanes. The strategy is also useful to gain access to oxa- and azatriquinanes, which incorporate the spiroindoline moiety. The method is further extended to the synthesis of lactone-bearing as well as uracil-fused angular triquinanes.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-10-16T13:46:39Z
2014-10-16T13:46:39Z
2012
 
Type Article
 
Identifier ORGANIC LETTERS, 14(21)5476-5479
http://dx.doi.org/10.1021/ol302557a
http://dspace.library.iitb.ac.in/jspui/handle/100/15702
 
Language en