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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/3783

Title: Cycloaddition of cyclohexa-2,4-dienones, ring-closing metathesis, and photochemical reactions: A common stereoselective approach to duprezianane, polyquinane and sterpurane frameworks
Authors: SINGH, V
PRAVEENA, GD
KARKI, K
MOBIN, SM
Keywords: 1st total-synthesis
di-pi-methane
fungus stereum-purpureum
diels-alder reactions
organic-synthesis
natural-products
chemoenzymatic synthesis
periodate oxidation
olefin-metathesis
linear triquinane
Issue Date: 2007
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY, 72(6), 2058-2067
Abstract: 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.
URI: http://dx.doi.org/10.1021/jo062416m
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3783
http://hdl.handle.net/10054/3783
ISSN: 0022-3263
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