Efficient enantioselective syntheses of chloramphenicol and (d)-threo- and (d)-erythro-sphingosine
β 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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β¦ 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.
π SIMILAR VOLUMES
## Isolated vield. \*) The free amine bases 1 4 are prone to air-oxidation and are difficult to handle.
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