Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine

Richard J B H N van den Berg; Cornelius G N Korevaar; Herman S Overkleeft; Gijsbert A van der Marel; Jacques H van Boom

doi:10.1021/jo049277y

Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine

J Org Chem. 2004 Aug 20;69(17):5699-704. doi: 10.1021/jo049277y.

Authors

Richard J B H N van den Berg¹, Cornelius G N Korevaar, Herman S Overkleeft, Gijsbert A van der Marel, Jacques H van Boom

Affiliation

¹ Cosmoferm B.V., P.O. Box 386, 2600 AJ Delft, The Netherlands.

PMID: 15307742
DOI: 10.1021/jo049277y

Abstract

The synthesis of naturally occurring D-erythro-(2R,3S,4E)-sphingosine from commercially available D-ribo-(2S,3S,4R)-phytosphingosine is described. The key step in the reaction sequence comprises TMSI/DBN promoted regio- and stereoselective oxirane opening of intermediate 2-phenyl-4-(S)-[(1S,2S)-1,2-epoxyhexadecyl]-1,3-oxazoline followed by the in situ trans-elimination of 2-phenyl-4-(S)-[(1S,2R)-1,2-dideoxy-2-iodo-1-trimethylsilyloxyhexadecyl]-1,3-oxazoline.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Brain
Catalysis
Indicators and Reagents
Molecular Structure
Sphingosine / analogs & derivatives*
Sphingosine / chemical synthesis*
Sphingosine / chemistry*
Stereoisomerism

Substances

Indicators and Reagents
erythro-(2R,3S)-sphingosine
phytosphingosine
Sphingosine