37 大環状ペプチド抗生物質エキノカンジン類の合成研究

概要

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Approaches to the total synthesis of echinocandin C(2), a 21-membered cyclic hexapeptide antibiotic isolated from Aspergillus ruglosus, have been described. The syntheses of four unusual amino acid moieties 3, 4, 5, and 6 in echinocandin C were carried out mainly from the allylglycine derivative and/or the vinylglycine equivalent in an efficient manner via a stereoselective introduction of β- or γ-hydroxyl group. The acyclic hexapeptide of echinocandin C, cleaved at the amide acetal part, was constructed as described in the followings. Synthesis of the left half was achieved by the use of a newly developed trimethylsilylimidazol method; The threonine moiety 33 , an amino acid free form, was condensed with the pyridine thiol ester 32 in an one-pot. 4-Hydroxy-L-proline(5) was connected with 39 by trimethylsilylimidazol/triethylamine. These peptide moieties were condensed with DEPC to the pentapeptide 41. Finally, 43 was condensed with 42 using DEPC to the hexapeptide 44. The cyclization step to echinocandin C is in progress.
天然有機化合物討論会の論文
1985-09-07