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Molecular diversity from aromatics. Cycloaddition of cyclohexa-2,4-dienones, ring-closing metathesis and sigmatropic shifts: a general and stereoselective route to novel spirocarbocyclics

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Title Molecular diversity from aromatics. Cycloaddition of cyclohexa-2,4-dienones, ring-closing metathesis and sigmatropic shifts: a general and stereoselective route to novel spirocarbocyclics
 
Creator SINGH, V
DAS, B
JARHAD, DB
MOBIN, SM
 
Subject CATALYTIC ASYMMETRIC-SYNTHESIS
DIELS-ALDER REACTIONS
ORGANIC-SYNTHESIS
CLAISEN REARRANGEMENT
STEREOCONTROLLED SYNTHESIS
SPIROCYCLIC COMPOUNDS
OLEFIN-METATHESIS
NATURAL-PRODUCTS
CONSTRUCTION
TRIQUINANES
Oxidative dearomatization
Diels-Alder reaction
Cyclohexa-2,4-dienone
Ring-closing metathesis
Oxa-di-pi-methane rearrangement
1,3-Acylshift
 
Description A novel, general and stereoselective route to spiroannulated bicyclo[2.2.2]octenones and their transformation to spiroannulated bicyclo[3.3.0]- and bicyclo[4.2.0]octanes is described. Oxidative dearomatization of o-hydroxymethylphenols, cycloaddition of spiroepoxycyclohexadienones, ring-closing metathesis and photochemical sigmatropic 1,2- and 1,3-acyl shifts are the key features of our methodology. (C) 2014 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2016-01-15T05:51:31Z
2016-01-15T05:51:31Z
2015
 
Type Article
 
Identifier TETRAHEDRON, 71(4)560-576
0040-4020
http://dx.doi.org/10.1016/j.tet.2014.12.033
http://dspace.library.iitb.ac.in/jspui/handle/100/17860
 
Language en