Journal
TETRAHEDRON LETTERS
Volume 46, Issue 9, Pages 1419-1421Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.01.030
Keywords
DMA; 2 '-deoxymugineic acid; reductive alkylation; reduced peptide bond
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A short and practical synthesis of 2'-deoxymugineic acid (DMA) has been developed via reductive alkylation with the aldehyde intermediates. No protection of azetidine-2-carboxylic acid was required and the presence of free carboxylic acid function facilitated purification by simple acid and base extractions. Furthermore, the intermediates were conveniently purified by HPLC due to the presence of chromophoric benzyl ester protecting group(s). Hydrogenolysis of the benzyl protecting groups in the final step furnished DMA in overall good yield. (C) 2005 Elsevier Ltd. All rights reserved.
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