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Determination of the relative stereochemistry of 5α‐ and 5β‐diastereomers of [2α,3β,3aα]‐ethyl hexahydro‐2‐ (1,2,3,4‐ tetraacetoxybutyl)‐ 5,6,6‐ trimethylpyrrolo[1,2‐ b ] isoxazole‐3‐ carboxylate
Author(s) -
Vasu J.,
Nadkarni Pradeep J.,
Trivedi Girish K.,
Steigel Alois
Publication year - 1991
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260290702
Subject(s) - chemistry , diastereomer , isoxazole , stereochemistry , benzene , proton nmr , carboxylate , medicinal chemistry , organic chemistry
(±)‐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‐dideoxy‐ L (−)‐arabinoheptenoate in anhydrous benzene to give a mixture of two diastereomeric isoxazolidines, [2α,3β,3aα,5α]‐ and [2α,3β,3aα,5β]‐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 ( 1 H– 1 H) COSY, ( 13 C– 1 H) HETCOR and NOEDS techniques.