| 张桂铭.海洋天然产物brevianamide K的全合成[J].中国海洋药物,2023,42(3):57-63. |
| 海洋天然产物brevianamide K的全合成 |
| Total synthesis of marine natural product brevianamide K |
| 投稿时间：2022-03-19 修订日期：2022-04-22 |
| DOI：10.13400/j.cnki.cjmd.2023.03.004 |
| 中文关键词: brevianamide K 吲哚二酮哌嗪生物碱 羟醛缩合 |
| English Keywords:brevianamide K indole diketopiperazine alkaloid aldol condensation |
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| 中文摘要: |
| 摘 要：目的 对海洋曲霉菌的次级代谢产物brevianamide K进行全合成研究，旨在解决其天然来源有限的问题，进而为其生物活性、作用机制的进一步研究以及同家族其他化合物的合成奠定基础。方法 以N-Pht-甘氨酸为起始原料，通过酰化、去保护、胺酯交换、乙酰基保护反应得到羟醛缩合反应的1个片段。以吲哚为起始原料，通过氯代、取代、Vilsmeier-Haack反应、保护基保护得到另1个片段。2个片段发生羟醛缩合反应后脱除保护基完成目标分子的全合成。结果 从商业可得化合物出发，通过最长线性7步反应，以9%的总收率完成brevianamide K的首次全合成，为后续活性研究和同家族其他化合物的合成奠定了基础。
关键词：brevianamide K；吲哚二酮哌嗪生物碱；羟醛缩合 |
| English Summary: |
| Abstract: Objective The total synthesis of brevianamide K, a secondary metabolite of Marine Aspergillus aspergillus, was carried out in order to solve the problem of its limited natural sources and lay a foundation for further studies on its biological activity and mechanism as well as the synthesis of other compounds in the same family. Methods Using N-Phthaloylglycine as starting material, a fragment of Aldol condensation reaction was obtained by acylation, deprotection, amine ester exchange reaction and acetyl group protection. With indole as starting material, another fragment was obtained by chlorination, substitution, Vilsmeier-Haack reaction and MOM protection. After the two fragments underwent Aldol condensation reaction, the MOM protective group was removed to complete the synthesis of the target molecule. Results Brevianamide K was synthesized for the first time at 9% overall yield through 7 steps from commercially available compounds, which laid a foundation for the subsequent activity studies and the synthesis of other compounds in the same family.
Key words：brevianamide K; indole diketopiperazine alkaloid; aldol condensation |
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