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Cycloaddition of cyclohexa-2,4-dienones, ring-closing metathesis, and photochemical reactions: A common stereoselective approach to duprezianane, polyquinane and sterpurane frameworks

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Title Cycloaddition of cyclohexa-2,4-dienones, ring-closing metathesis, and photochemical reactions: A common stereoselective approach to duprezianane, polyquinane and sterpurane frameworks
 
Creator SINGH, V
PRAVEENA, GD
KARKI, K
MOBIN, SM
 
Subject 1st total-synthesis
di-pi-methane
fungus stereum-purpureum
diels-alder reactions
organic-synthesis
natural-products
chemoenzymatic synthesis
periodate oxidation
olefin-metathesis
linear triquinane
 
Description A novel approach to three different types of carbocyclic frameworks belonging to dupreziananes, sterpuranes, and polyquinanes from simple aromatic precursors has been presented. Cycloaddition of appropriately appended cyclohexa-2,4-dienones with acyclic dienes gave bridged bicyclic octanes suitably disposed with olefinic chains, which upon ring-closing metathesis led to functionalized tricyclo[5.2.2.0(1,5)]undecanes related to dupreziananes. Photochemical sigmatropic 1,2- and 1,3-acyl shifts in tricyclo[5.2.2.0(1,5)] undecanes upon triplet and singlet excitation provided stereoselective routes to sterpurane and polyquinane frameworks.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-13T22:06:44Z
2011-12-26T12:48:09Z
2011-12-27T05:45:37Z
2011-07-13T22:06:44Z
2011-12-26T12:48:09Z
2011-12-27T05:45:37Z
2007
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 72(6), 2058-2067
0022-3263
http://dx.doi.org/10.1021/jo062416m
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3783
http://hdl.handle.net/10054/3783
 
Language en