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A tandem enyne/ring closing metathesis approach to the synthesis of novel angularly fused dioxa-triquinanes

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Title A tandem enyne/ring closing metathesis approach to the synthesis of novel angularly fused dioxa-triquinanes
 
Creator KALIAPPAN, KRISHNA P
NANDURDIKAR, RAHUL S
SHAIKH, MOBIN M
 
Subject triquinanes
dioxa-triquinanes
grubb's catalyst
carbohydrates
 
Description Triquinanes and their oxygenated congeners, oxa- and dioxa-triquinanes, exhibit versatile biological activities in conjunction with synthetically challenging molecular architecture. Owing to these properties, several new strategies have been developed to accomplish the synthesis of these sesquiterpenes. Among the new strategies, cascade radical cyclization strategy has been broadly explored and well studied. Herein, we report our efforts in detail for the synthesis of dioxa-triquinanes using a domino enyne/RCM strategy as the key step. Carbohydrate based synthesis not only allows the use of inexpensive and optically pure starting materials, but also the furanose derivatives, which already possess one of the requisite dihydro-furan moieties in the desired dioxa-triquinane. The other two five-membered rings were constructed simultaneously by the cascade enyne/RCM reaction using the Grubbs' second-generation catalyst. During the course of our synthesis it was observed that the acetonide protection hinders the RCM reaction, after the initial enyne metathesis reaction. The reaction underwent smoothly under argon atmosphere, whilst use of ethylene atmosphere was found to hinder the formation of the tandem enyne/RCM product. The effect of substitution on the key reaction is described here.
 
Publisher Elsevier
 
Date 2009-02-21T11:30:00Z
2011-11-25T17:21:28Z
2011-12-26T13:06:00Z
2011-12-27T05:51:53Z
2009-02-21T11:30:00Z
2011-11-25T17:21:28Z
2011-12-26T13:06:00Z
2011-12-27T05:51:53Z
2006
 
Type Article
 
Identifier Tetrahedron 62(21), 5064-5073
0040-4020
http://dx.doi.org/10.1016/j.tet.2006.03.046
http://hdl.handle.net/10054/734
http://dspace.library.iitb.ac.in/xmlui/handle/10054/734
 
Language en