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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|
|Authors: ||SINGH, V|
|Keywords: ||1st total-synthesis|
|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[18.104.22.168(1,5)]undecanes related to dupreziananes. Photochemical sigmatropic 1,2- and 1,3-acyl shifts in tricyclo[22.214.171.124(1,5)] undecanes upon triplet and singlet excitation provided stereoselective routes to sterpurane and polyquinane frameworks.|
|Appears in Collections:||Article|
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