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Intramolecular cycloaddition in cyclohexa-2,4-dienone and photochemical reactions: An efficient route to azatriquinane and azasterpurane frameworks

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Title Intramolecular cycloaddition in cyclohexa-2,4-dienone and photochemical reactions: An efficient route to azatriquinane and azasterpurane frameworks
 
Creator SINGH, V
SAHU, BC
MOBIN, SM
 
Subject cascade radical cyclizations
1st total-synthesis
organic-synthesis
carbene complexes
linear triquinane
natural-products
chemistry
acid
sesquiterpenes
polyquinanes
cyclohexa-2,4-dienone
cycloaddition
oxa-di-pi-methane rearrangement
1,3-acyl shift photochemistry
 
Description A novel, efficient and stereoselective entry to azatriquinane and azasterpurane frameworks from simple aromatic precursor, is described. The methodology involves in situ generation of cyclohexa-2,4-dienones containing a tether and intramolecular pi 4s+pi 2s cycloaddition that leads to a bicyclo[2.2.2]octenone-annulated five-membered ring that contains nitrogen. Further manipulation of the resulting adduct followed by photochemical sigmatropic shifts readily furnished the azatriquinane and azasterpurane frameworks.
 
Publisher GEORG THIEME VERLAG KG
 
Date 2011-07-30T08:27:42Z
2011-12-26T12:52:44Z
2011-12-27T05:39:36Z
2011-07-30T08:27:42Z
2011-12-26T12:52:44Z
2011-12-27T05:39:36Z
2008
 
Type Article
 
Identifier SYNLETT, (8), 1222-1224
0936-5214
http://dx.doi.org/10.1055/s-2008-1072588
http://dspace.library.iitb.ac.in/xmlui/handle/10054/7902
http://hdl.handle.net/10054/7902
 
Language en