Stereoselective synthesis of L-[2,3,4,5-D4] ornithine

Synthesis of L-[2,3,4,5-D-4]ornithine in which all of the diastereotopic hydrogens were stereoselectively labeled with deuterium was investigated. The chirally deuterated 3-aminopropanal derivative. a key intermediate in this synthesis, was prepared by a catalytic deuteration of an unsaturated gamma-lactone derived for L-glutamic acid followed by several functional group interconversions, Condensation or the obtained deuterium-labeled 3-aminopropanal derivative with a chiral glycine template afforded unsaturated ornithine. The dehydroornithine was then subjected to a catalytic deuteration followed by deprotection to give the L-[2,3,4,5-D-4]ornithine. Copyright (C) 2002 John Wiley Sons, Ltd.