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Efficient enantioselective syntheses of chloramphenicol and (d)-threo- and (d)-erythro-sphingosine

✍ Scribed by E.J. Corey; Soongyu Choi


Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
130 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis


The chiral diazaborolidine 1 has been applied to the enantioselective syntheses of chloramphenicol ( 2) and (D)-threo-N-acetylsphingosine (3), a synthetic precursor of the diastereomeric (D)-sphingosines.


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In their synthesis of dihydrosphingosine, Rozrsh and Adum [ 131 observed the formation of a I :1 mixture of two isomeric oxazolidinones resulting from an intramolecular transacylation: under our conditions, however, only 9 was obtained. We thank Prof. Dr. W . Roush for a preliminary communication of