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Aromatics to Diquinanes: An Expeditious Synthesis of Tetramethylbicyclo[3.3.0]octane Framework of Ptychanolide

DSpace at IIT Bombay

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Title Aromatics to Diquinanes: An Expeditious Synthesis of Tetramethylbicyclo[3.3.0]octane Framework of Ptychanolide
 
Creator SINGH, V
CHANDRA, G
MOBIN, SM
 
Subject liverwort frullanoides-densifolia
ptychanthus-striatus lehm
1st total-synthesis
molecular complexity
linear triquinane
organic-synthesis
natural-products
building-blocks
lindenb nees
rearrangement
cycloaddition
oxa-di-pi-methane rearrangement
diquinanes
diels-alder reaction
 
Description An expeditious route to methyl-7-oxo-1,4,5,8-tetramethylbicyelo[3.3.0]octane-3-carboxylate from a simple aromatic precursor is described. Oxidative dearomatization of 2-hydroxymethyl-3,4,6-trimethylphenol into spiroepoxycycloliexa-2,4-dierone, its cycloaddition and triplet-sensitized 1,2-acyl shift, and stereochemical inversion are the key features Of Our methodology.
 
Publisher GEORG THIEME VERLAG KG
 
Date 2011-07-30T08:09:26Z
2011-12-26T12:52:44Z
2011-12-27T05:39:35Z
2011-07-30T08:09:26Z
2011-12-26T12:52:44Z
2011-12-27T05:39:35Z
2008
 
Type Article
 
Identifier SYNLETT, (20), 3111-3114
0936-5214
http://dx.doi.org/10.1055/s-0028-1087275
http://dspace.library.iitb.ac.in/xmlui/handle/10054/7897
http://hdl.handle.net/10054/7897
 
Language en