抗疟海洋天然产物 Albopunctatone 的全合成。

Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone.

机构信息

Discovery Biology, Griffith Institute for Drug Discovery , Griffith University , Nathan , Queensland , Australia.

Tuberculosis Research Laboratory, School of Chemistry and Molecular Biosciences , University of Queensland , Brisbane , Australia.

出版信息

Org Lett. 2019 Jul 19;21(14):5519-5523. doi: 10.1021/acs.orglett.9b01838. Epub 2019 Jul 9.

DOI:10.1021/acs.orglett.9b01838

PMID:31287326

Abstract

The first approaches to the 10'-anthronyl-2-anthraquinone skeleton have been devised, allowing two syntheses of the marine natural product albopunctatone. Both routes involve regioselective addition of a nucleophilic masked anthraquinone to a protected chrysazin derivative; the best affords albopunctatone in five steps and 35% overall yield. Albopunctatone exhibits potent inhibitory activity against and negligible toxicity to a range of other microbial pathogens and mammalian cells.

摘要

已经设计出了 10'-蒽酮基-2-蒽醌骨架的初步方法，从而可以进行两种海洋天然产物 Albopunctatone 的合成。这两种方法都涉及亲核性掩蔽蒽醌对保护的 Chrysazin 衍生物的区域选择性加成；最佳途径以五步和 35%的总收率得到 Albopunctatone。Albopunctatone 对表现出强烈的抑制活性，对一系列其他微生物病原体和哺乳动物细胞几乎没有毒性。