98778-77-9Relevant academic research and scientific papers
Organic Chemistry of L-Tyrosine. 1. General Synthesis of Chiral Piperazines from Amino Acids
Jung, Michael E.,Rohloff, John C.
, p. 4909 - 4913 (2007/10/02)
A new method for the conversion of optically active diketopiperazines (cyclo-dipeptides) into optically pure piperazines is described.Due to poor solubility of certain cyclo-dityrosine derivatives, the usual method using lithium aluminum hydride reaction was problematic, giving racemization under forcing conditions.However, the use of borane/tetrahydrofuran for this diketopiperazine to piperazine reduction proceeded well, affording high yields of optically pure materials.In this manner several mixed cyclo-dityrosine derivatives 9a-d were transformed into the piperazines 10a-d, potentially useful intermediates for the synthesis of the antibiotic alkaloids, piperazinomycin (1) and herquline (2).Finally, the naturally occuring alkaloid isolated from Zanthoxylum arborescens, 7b was prepared by this route.
