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Synthesis of the Diastereomers of Dethiobiotin Using the Conjugate Addition of 4‐Phenyloxazolidin‐2‐one to a Nitroalkene
Author(s) -
Lucet Denis,
Heyse Philippe,
Gissot Arnaud,
Le Gall Thierry,
Mioskowski Charles
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200011)2000:21<3575::aid-ejoc3575>3.0.co;2-r
Subject(s) - nitroalkene , diastereomer , chemistry , conjugate , enantiomer , stereochemistry , salt (chemistry) , potassium , organic chemistry , enantioselective synthesis , catalysis , mathematical analysis , mathematics
Natural D ‐dethiobiotin and its three stereoisomers were prepared from a single nitroalkene 2 . Conjugate addition of the potassium salt of ( R )‐4‐phenyloxazolidin‐2‐one 3 to 2 led to two diastereomeric nitro compounds 6 and 7 . Their enantiomers were prepared from ( S )‐ 3 . These compounds were converted in three analogous steps into the dethiobiotin isomers as their methyl esters.