A Total Synthesis of the Cyclic Depsipeptide Chaiyaphumine‐A
Copyright policy )A Total Synthesis of the Cyclic Depsipeptide Chaiyaphumine‐A
Abstract The first total synthesis of Chaiyaphumine‐A, a cyclic depsipentapeptide isolated from Xenorhabdus SP. PB614 which showed good activity against Plasmodium falcifarum (IC 50 = 0.61 μM) has been described. The synthesis of Chaiyaphumine‐A was accomplished by solution phase fragment synthesis using protection, deprotection, coupling and cyclisation reactions. Five amino acids viz . L‐Threonine, D‐phenyl alanine, D‐Alanine, L‐Proline and L‐Tryptophan are assembled together by amide coupling reactions. The macrocylization of side chain (‐OH) of L‐ β Thr and C‐terminus of carboxylic acid from L‐Tryptophan to give Chaiyaphumine‐A in 12% yield. The spectroscopic data ( 1 H‐NMR, 13 C‐NMR, HRMS) confirmed the structure elucidation as reported in literature.
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