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Synthesis and photoreaction of tricyclo[5.2.2.0(2,6)]undecanes in the excited singlet (S-1) state: a novel and stereospecific route to protoilludanoids

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Title Synthesis and photoreaction of tricyclo[5.2.2.0(2,6)]undecanes in the excited singlet (S-1) state: a novel and stereospecific route to protoilludanoids
 
Creator SINGH, V
SHARMA, U
 
Subject secondary mold metabolites
structure elucidation
armillaria-mellea
photochemistry
biosynthesis
fomannosin
illudol
beta
 
Description A novel and general approach to the synthesis of functionalised protoilludane skeletons having fused-four-, six-and five-membered rings is described, A photochemical sigmatropic 1,3-acyl shift in endo-tricyclo[5.2.2.0(2,6)]-undecanes having a beta,gamma-unsaturated carbonyl chromophore, and pi(4s) + pi(2s) cycloaddition of spiro[cyclohexa-2,4-diene-oxiran]-6-one are the key features of this approach, An efficient one-step synthesis of the epoxy ketone 11 by pi(4s) + pi(2S) cycloaddition of the in situ generated spiro[cyclohexa-2,4-diene-oxiran]one is reported, Further transformation of 11 to a variety of endo-tricyclo[5.2.2.0(2,6)]-undecanes (20, 25, 28, 30 and 31) and their photochemical behaviour upon singlet (S-1) excitation is described, Direct excitation of all the tricyclic chromophoric systems in benzene neatly furnished the protoilludanoids 32-36.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2011-08-28T20:31:04Z
2011-12-26T12:58:12Z
2011-12-27T05:47:44Z
2011-08-28T20:31:04Z
2011-12-26T12:58:12Z
2011-12-27T05:47:44Z
1998
 
Type Article
 
Identifier JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, (2), 305-312
0300-922X
http://dx.doi.org/10.1039/a704817c
http://dspace.library.iitb.ac.in/xmlui/handle/10054/11836
http://hdl.handle.net/10054/11836
 
Language en