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Molecular complexity from aromatics: A novel, stereoselective route to tricyclo[5.2.2.0(1,5)]undecenones, tricyclo[6.2.2.0(1,6)]dodecenones, and [n.3.3]propellanes

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Title Molecular complexity from aromatics: A novel, stereoselective route to tricyclo[5.2.2.0(1,5)]undecenones, tricyclo[6.2.2.0(1,6)]dodecenones, and [n.3.3]propellanes
 
Creator SINGH, V
SAHU, PK
SINGH, RB
MOBINT, SM
 
Subject 1st total-synthesis
fischer carbene complexes
taxus-canadensis needles
pi-methane rearrangement
excoecaria-agallocha l
natural-products
chemoenzymatic synthesis
photochemical-reactions
cascade rearrangements
cyclization reactions
 
Description A general stereoselective route to functionalized and substituted tricyclo [5.2.2.0(1,5)] undecenones, tricyclo[6.2.2.0(1,6)]dodecenones, and [3.3.3]- and [4.3.3]propellanes from simple aromatic precursors is reported. The methodology involves generation and cycloaddition of annulated cyclohexa-2,4-dienones with various acrylates followed by manipulation of the resulting tricyclic adducts, leading to functionalized tricyclo[5.2.2.0(1,5)] undecenones and tricyclo[6.2.2.0(1.6)]dodecenones endowed with a beta,gamma-enone chromophore. Photochemical reaction of the tricyclic chromophoric systems followed by reductive cleavage provided an efficient entry into propellanes.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-14T12:55:02Z
2011-12-26T12:48:23Z
2011-12-27T05:35:51Z
2011-07-14T12:55:02Z
2011-12-26T12:48:23Z
2011-12-27T05:35:51Z
2007
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 72(26), 10155-10165
0022-3263
http://dx.doi.org/10.1021/jo702168s
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3958
http://hdl.handle.net/10054/3958
 
Language en