72635-82-6Relevant articles and documents
Synthetic Studies on Antifungal Cyclic Peptides, Echinocandins. Stereoselective Total Synthesis of Echinocandin D via a Novel Peptide Coupling
Kurokawa, Natsuko,Ohfune, Yasufumi
, p. 6195 - 6222 (2007/10/02)
Synthetic studies on the novel fungicidal oligopeptides, echinocandins (1b and 1c), are described.The constituent amino acids 5-8 were synthesized in a stereocontrolled manner from the chiral starting materials, 5a, 6a and 7a, respectively.The coupling of these amino acids was characterized by the use of unprotected amino acid as the C-terminal and 2-pyridyl thiol ester as the N-terminal, and the coupling was performed in the presence of 1-(trimethylsilyl)imidazole (TMSIm) or a catalytic amount of tert-amine to give C-terminal free dipeptides, 14 and 16a, respectively, which were converted to the pentapeptide 17a, a common intermediate for the synthesis of 1b and 1c.The synthesis of 1c was achieved by the cyclization of the hexapeptide 24b.
