Enantioselective Synthesis of D-erythro-Sphingosine and of Ceramide
β Scribed by Radomir Julina; Thomas Herzig; Bruno Bernet; Andrea Vasella
- Publisher
- John Wiley and Sons
- Year
- 1986
- Tongue
- German
- Weight
- 398 KB
- Volume
- 69
- Category
- Article
- ISSN
- 0018-019X
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β¦ Synopsis
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 his results.
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π SIMILAR VOLUMES
2,4-Di-O-protected Pthreose, readily avaiZabZe from D-galactose, is a versatile intermediate for D-erythro-sphingosine syntheses via trans-selective Wittig reaction, azide introduction at the unprotected hydroxyZic group, and subsequent azide reduction.
D-erythro-Sphingosine 9 is a building block of cerebrosides and glycosphingolipids and was synthesized in 5 steps via an asymmetric aldol addition of the lithiated bislactim ether of cyclo-(L-Val-Gly) 4 to (2E)-hexadecenal(3) in an overall yield of 21 %. I.
D-erythro-sphingosine and D-esythro-sphinganine can be produced in protected form from serine by a synthetic approach in which the normal biological intermediate 3-ketosphinganine in protectyed form, is a key synthetic intermediate. The sequence is short and convergent, proceeds in good overall yiel