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DETERMINATION OF THE RELATIVE STEREOCHEMISTRY OF 5-ALPHA-DIASTEREOMER AND 5-BETA-DIASTEREOMER OF [2-ALPHA,3-BETA,3A-ALPHA]-ETHYL HEXAHYDRO-2-(1,2,3,4-TETRAACETOXYBUTYL)-5,6,6-TRIMETHYLPYRROLO[1,2-B]ISOXAZOLE-3-CARBOXYLATE

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Title DETERMINATION OF THE RELATIVE STEREOCHEMISTRY OF 5-ALPHA-DIASTEREOMER AND 5-BETA-DIASTEREOMER OF [2-ALPHA,3-BETA,3A-ALPHA]-ETHYL HEXAHYDRO-2-(1,2,3,4-TETRAACETOXYBUTYL)-5,6,6-TRIMETHYLPYRROLO[1,2-B]ISOXAZOLE-3-CARBOXYLATE
 
Creator VASU, J
NADKARNI, PJ
TRIVEDI, GK
 
Subject cyclo-addition
nitrones
isoxazolidine diastereomers
configurational assignment
regiochemical and stereochemical control
2d nmr
(h-1-h-1) cosy
(13c-1h) hetcor dept noeds
 
Description (+/-)-4,5,5-Trimethyl-1-pyrroline-1-oxide reacted readily with ethyl 4,5,6,7-tetra-O-acetyl-trans-2,3-dehydro-2,3-dehydro-2,3-dideoxy-L(-)-arabinohepotenoate in anhydrous benzene to give a mixture of two diastereomeric isoxazolidines, [2-alpha,3-beta,3a-alpha,5-alpha]- and [2-alpha,3-beta,3a-alpha,5-beta]-ethyl hexahydro-2-(1,2,3,4- tetraacetoxybutyl)-5,6,6-trimethylpyrrolo[1,2- b] isoxazole-3-carboxylate. The structures and configurations of both diastereomers were determined through the use of the (H-1-H-1) COSY, (C-13-H-1) HETCOR and NOEDS techniques.
 
Publisher JOHN WILEY & SONS LTD
 
Date 2011-08-16T20:01:10Z
2011-12-26T12:55:07Z
2011-12-27T05:43:43Z
2011-08-16T20:01:10Z
2011-12-26T12:55:07Z
2011-12-27T05:43:43Z
1991
 
Type Article
 
Identifier MAGNETIC RESONANCE IN CHEMISTRY, 29(7), 645-649
0749-1581
http://dx.doi.org/10.1002/mrc.1260290702
http://dspace.library.iitb.ac.in/xmlui/handle/10054/9607
http://hdl.handle.net/10054/9607
 
Language en