Synthesis of the Diastereomers of Dethiobiotin Using the Conjugate Addition of 4??Phenyloxazolidin??2??one to a Nitroalkene

D Lucet, P Heyse, A Gissot, T Le Gall…

Index: Lucet, Denis; Heyse, Philippe; Gissot, Arnaud; Le Gall, Thierry; Mioskowski, Charles European Journal of Organic Chemistry, 2000 , # 21 p. 3575 - 3579

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Citation Number: 12

Abstract

Abstract 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.