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Diversity-Oriented Approach to Normuscopyridine and Its Analogues through Ring-Closing Metathesis

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Title Diversity-Oriented Approach to Normuscopyridine and Its Analogues through Ring-Closing Metathesis
 
Creator KOTHA, S
WAGHULE, GT
SHIRBHATE, ME
 
Subject Macrocycles
Cyclophanes
Fragrances
Metathesis
Reduction
OLEFIN-METATHESIS
NOBEL LECTURE
CYCLOPHANE DERIVATIVES
CATALYTIC METATHESIS
KEY STEPS
MACROCYCLIZATION
MOLECULES
EFFICIENT
PRODUCTS
PROTOCOL
 
Description Ring-closing metathesis (RCM) is a useful protocol for assembling macrocycles. To synthesize normuscopyridine, and its analogues we used RCM as a key step in our strategy. Our approach to the synthesis of pyridine macrocycles involves two routes. The first approach starts with alkenylation of 2,6-bis[(phenylsulfonyl)methyl]pyridine and involves five steps with 10% overall yield. The second route begins with Grignard addition to pyridine-2,6-dicarbo nitrile, followed by RCM and one-pot removal of the carbonyl group before hydrogenation of the double bond in 28% overall yield. This approach has only three steps. Neither route involves the use of protecting groups. Various points of diversification are embedded in our strategy and eight different cyclophanes were assembled by adopting a general approach to these macrocyclics.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-12-28T11:18:24Z
2014-12-28T11:18:24Z
2014
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014(5)984-992
1434-193X
1099-0690
http://dx.doi.org/10.1002/ejoc.201301493
http://dspace.library.iitb.ac.in/jspui/handle/100/16339
 
Language English