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Diels-Alder Cycloaddition and Ring-Closing Metathesis: A Versatile, Stereoselective, and General Route to Embellished Bridged Bicyclic Systems, Carbocyclic Framework of Secoatisanes, and Homologues

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Title Diels-Alder Cycloaddition and Ring-Closing Metathesis: A Versatile, Stereoselective, and General Route to Embellished Bridged Bicyclic Systems, Carbocyclic Framework of Secoatisanes, and Homologues
 
Creator SINGH, V
SAHU, PK
SAHU, BC
MOBIN, SM
 
Subject homoallyl radical rearrangement
excoecaria-agallocha-l
double michael reaction
formal total-synthesis
olefin-metathesis
organic-synthesis
periodate oxidation
tricyclic core
atisane-type
platencin
 
Description A general and stereoselective methodology for the synthesis of bridged bicyclic octenones having various types of alkenyl chains and a tricyclic framework of secoatisanes and higher analogues is reported. In situ generation and cycloaddition of 2-allyl-6,6-spiroepoxycyclohexadienones with ethyl acrylate gave bicyclo[2.2.2]octanes having an allyl group at the bridgehead and other chemically distinguishable functionality in a regio- and stereoselective fashion. Selective manipulation of adducts led to the introduction of other olefinic chain of variable lengths at the carbon adjacent to the bridge head. Ring-closing metathesis in bicyclooctanes having olefin tethers provided an efficient route to tricyclic systems having bicyclo[2.2.2]octane framework having spiro-fused six-, seven-, and eight-membered rings.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-13T23:05:45Z
2011-12-26T12:47:26Z
2011-12-27T05:52:20Z
2011-07-13T23:05:45Z
2011-12-26T12:47:26Z
2011-12-27T05:52:20Z
2009
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 74(16), 6092-6104
0022-3263
http://dx.doi.org/10.1021/jo901279g
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3796
http://hdl.handle.net/10054/3796
 
Language en