Synthesis of enantiomerically and diastereomerically pure 2(S)-amino-6(R)-hydroxy-1,7-heptanedioic acid dimethyl ester hydrochloride from cycloheptadiene.
The complete carbon framework of enantiomerically and diastereomerically pure 2(S)-amino-6(R)-hydroxy-1,7-heptanedioic acid dimethyl ester hydrochloride was derived from cycloheptadiene in six steps utilizing an amino acid-derived acylnitroso Diels-Alder reaction as the key step. This versatile amino diester has been previously used to synthesize amino-differentiated diaminopimelic acid (DAP) and biologically active analogues. In addition, after formation of a novel aminoxy diketopiperazine, the newly formed carboxyl groups were differentiated by a novel transpeptidation of the amino acid that directed the stereochemistry of the initial cycloaddition.
Shireman
B T
BT
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Miller
M J
MJ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002473:Cell Wall / Q000737:chemistry; D003960:Diaminopimelic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006090:Gram-Negative Bacteria / Q000737:chemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D003960:Diaminopimelic Acid