Potential intermediates for incorporation of polyhydroxylated prolines into combinatorial libraries

Journal article

Bicyclic 2 and monocyclic 6 2-amino-1,4-lactones provide divergent intermediates for subsequent incorporation of polyhydroxylated prolines into combinatorial amide libraries. The X-ray crystal structure of an azidolactone, combined with molecular modelling, rationalises the very different behaviour of two azidolactones which are epimeric at a remote side- chain carbon. The conversion of 2 and 6 into DGDP 4 secures the structural claims in the paper. The enantiomers of 2 and 6 may provide access to libraries of potential inhibitors of UDP-Gal mutase and thus of mycobacterial cell wall biosynthesis.

Authors: Long, D; Frederiksen, S; Marquess, D; Lane, A; Watkin, D

• Publication status: Published
• Journal: TETRAHEDRON LETTERS
• Volume: 39
• Issue: 33
• Pages: 6091-6094
• Publication date: 1998-08-13
• DOI: 10.1016/S0040-4039(98)01256-8
• ISSN: 0040-4039
• Language: English