Synthesis of Optically Active 2-Piperidylglycine

Both chiral fhreo-and erythro-2-piperidylglycines were synthesized from racemic 2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethoic acid.(4S,5S)-4-Methyl-5-phenyl-2-oxa-zolidinone was used as a chiral auxiliary in the resolution and azidation.Many of a,pdiamino acids have displayed various biological activities.' Streptolntin [I, 2-amino-2-(5chloropiperidin-2-yljethanoic acid], one of a,pdiamino acids, is the parent amino acid of antitumor agent DKP 593A (2).The agent was isolated from the soil microorganism, Streptomyces griseoluteus and reported to he effective against certain solid The antitumor agent has been synthesized as a racemic mixture."treptolutinehas three chiral centers whose configurations are (R) at C-2', (S) at C-5' and C-2, thus the stereochemical relationship between C-2' and C-5' is trans, and that of C-2' and C-2 is fhreo.In the attempted synthesis of streptolutin, the corresponding eyfhro isomer was formed as a major compound.'2-Piperidylglycine [3, 2-amino-2-(piperidin-2-yl)ethanoic acid] has been studied as a model compound in the preparation of analogs of streptolutin and DKP 593A.6-8Heating 7-amino-7-carboxy-8-0x0-1azabicyclo[4.2.0]octane in 5 M HC1 gave a 2:l mixture of threo-and evfhro-2-piperdylglycines.' Hydrogenation of ethyl 2-piperidinylidene-N-(ethoxycarbonyl)glycinate on 10% PdK gave the corresponding erythro-glycine derivative.'