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An approach towards the total synthesis of (+)-epiquinamide and (+)-α-conhydrine from Garner aldehyde

IR@CDRI: CSIR-Central Drug Research Institute, Lucknow

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Field Value
 
Creator Srivastava, A K
Das, S K
Panda, Gautam
 
Date 2010-09-09T08:52:00Z
2010-09-09T08:52:00Z
2009
 
Identifier Tetrahedron, 65, 2009, 5322–5327
http://hdl.handle.net/123456789/586
 
Description A short and stereoselective route for the synthesis of 1-hydroxyquinolizidine, an advanced synthetic intermediate for the total synthesis of (+)-epiquinamide is presented. The key synthetic steps involve diastereoselective nucleophilic addition on L-serine derived Garner aldehyde and acid mediated (PTSA) ring closing metathesis. The methodology is also elaborated successfully for the total synthesis of (+)-α-conhydrine an important piperidine alkaloid.
 
Format 262839 bytes
application/pdf
 
Language en
 
Subject quinolizidine
indolizidine
piperidine
1-hydroxyquinolizidine
Conium maculatum
epipedobates tricolor
 
Title An approach towards the total synthesis of (+)-epiquinamide and (+)-α-conhydrine from Garner aldehyde
 
Type Article