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Molecular diversity from aromatics. A tandem oxidative dearomatization, cycloaddition and reactivity modulation in excited states: synthesis of tricyclo[5.3.1.0(1,5)]undecanes and bicyclo[4.2.0]octanes from common precursors

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Title Molecular diversity from aromatics. A tandem oxidative dearomatization, cycloaddition and reactivity modulation in excited states: synthesis of tricyclo[5.3.1.0(1,5)]undecanes and bicyclo[4.2.0]octanes from common precursors
 
Creator SINGH, V
ISLAM, SN
MALI, J
 
Subject Oxidative dearomatization
Cyclohexa-2,4-dienones
pi(4)s+pi(2)s cycloaddition
Oxa-di-pi-methane rearrangement
1,3-Acyl shift
Ring-closing metathesis
PALLADIUM-CATALYZED CYCLOALKENYLATION
RING-CLOSING METATHESIS
ORGANIC-SYNTHESIS
CYCLOHEXADIENONE KETALS
STEREOSELECTIVE ROUTE
NATURAL-PRODUCTS
TRICYCLOILLICINONE
REARRANGEMENT
CONSTRUCTION
(+/-)-STERPURENE
 
Description Stereoselective route to tricyclo[5.3.1.0(1,5)]undecane and bicyclo[4.2.0]octane ring systems present in the molecular structure of tricycloillicinone, cedrenoids and endiandric acid, elysiapyrones, respectively, is described. A tandem oxidative dearomatization of o-hydroxymethylphenol, pi(4)s+pi(2)s cycloaddition, reactivity modulation in excited state and ring-closing metathesis are the key features of our approach. (c) 2013 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-10-14T17:48:47Z
2014-10-14T17:48:47Z
2013
 
Type Article
 
Identifier TETRAHEDRON, 69(42)8865-8871
http://dx.doi.org/10.1016/j.tet.2013.08.015
http://dspace.library.iitb.ac.in/jspui/handle/100/14608
 
Language en