An efficient RCM-based synthesis of orthogonally protected meso-DAP and FK565.
A condensation--ring-close--ring-open sequence was employed for the synthesis of orthogonally protected meso-2,6-diaminopimelic acid, starting from easily accessible chiral synthons. Condensation of suitably protected L-allylglycine and D-vinylglycinol derivatives was followed by Grubbs' ring-closing metathesis to generate the key lactam intermediate. This strategy has been applied to a concise total synthesis of the potent immunostimulatory peptide FK565.
Del Valle
Juan R
JR
Department of Chemistry and Biochemistry, University of California-San Diego, La Jolla, CA 93027, USA. jdvalle@ucsd.edu
Goodman
Murray
M
D003500:Cyclization; D003960:Diaminopimelic Acid / Q000138:chemical synthesis*; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis*
D009842:Oligopeptides; D003960:Diaminopimelic Acid; C039537:heptanoyl-gamma-D-glutamyl-L-meso-diaminopimelyl-D-alanine