SYNTHESIS OF 2-CARBOXY-SUBSTITUTED SPHINGOSINE DERIVATIVES

From the sphingosine biosynthesis pathway it is deduced that 2-carboxy-substituted sphinganine derivatives should be suitable inhibitors of sphingosine biosynthesis. For their synthesis enantioselective acylation and a-hydroxy-alkylation of serine was performed via its optically pure 2-tert-butyl-oxazolidine derivatives 4A, B and ent-4A, known to undergo partial chirality transfer from serine to the 2-position of 4 and then to the 4-position. Thus, after acid hydrolysis compounds R-7Aa, -7Ab, -7Ac, -7Bb, S-7Aa, -7Ab, and 11 are provided highly stereoselectively. © 1990, Taylor & Francis Group, LLC. All rights reserved.