A short stereocontrolled synthesis of hydroxyethylene dipeptide isosteres
作者:D. Michael Jones、Bo Nilsson、Michael Szelke
DOI:10.1021/jo00060a052
日期:1993.4
A stereocontrolled synthesis of protected hydroxyethylene dipeptide isosteres 14 and 16 is described. It provides the 2R,4S,5S epimers required for the preparation of aspartic proteinase inhibitors. The choice of a benzene ring as a precursor to the carboxylic acid function has enabled us to use the readily accessible chiral Grignard reagent 3 which reacts with the protected alpha-amino aldehyde 8 stereoselectively. Kilogram quantities of 16 have been produced by this route in a satisfactory overall yield. The combination of N- and 0-protecting groups employed facilitates the incorporation of 14 or 16 into peptide-based enzyme inhibitors.
KARLSSON, J. OLLE;LUNDBLAD, ANITA;MALM, BENGT;NILSSON, INGEMAR;NITENBERG,+, TETRAHEDRON LETT., 30,(1989) N0, C. 2653-2656
作者:KARLSSON, J. OLLE、LUNDBLAD, ANITA、MALM, BENGT、NILSSON, INGEMAR、NITENBERG,+
DOI:——
日期:——
KARLSSON, JAN O.;SOHTELL, ERIK M. H.;STARKE, CARL I.;WESTERLUND, ROLF CH.
作者:KARLSSON, JAN O.、SOHTELL, ERIK M. H.、STARKE, CARL I.、WESTERLUND, ROLF CH.
DOI:——
日期:——
Synthesis of a new sulfur-containing dipeptide analogue