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环轮烷卡明 A 和 A,来自刚果弯管安息香藤本植物的含氧桥萘基异喹啉二聚体。

Cyclombandakamines A and A, Oxygen-Bridged Naphthylisoquinoline Dimers from a Congolese Ancistrocladus Liana.

机构信息

Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.

Faculté des Sciences, Université de Kinshasa , B.P. 202 Kinshasa XI, Democratic Republic of the Congo.

出版信息

Org Lett. 2017 Mar 17;19(6):1342-1345. doi: 10.1021/acs.orglett.7b00209. Epub 2017 Feb 23.

DOI:10.1021/acs.orglett.7b00209
PMID:28231014
Abstract

Cyclombandakamines A (1) and A (2), both with an unprecedented pyrane-cyclohexenone-dihydrofuran sequence and six stereocenters and two chiral axes, are the first oxygen-bridged dimeric naphthylisoquinoline alkaloids. They were isolated from the leaves of an as yet unidentified Congolese Ancistrocladus species. Their stereostructures were established by spectroscopic, chemical, and chiroptical methods in combination with DFT and TDDFT calculations. They apparently originate from a cascade of oxidative cyclization reactions of "open-chain" naphthylisoquinoline dimers and exhibit significant antiprotozoal activities.

摘要

环棒木卡明 A(1)和 A(2)均具有前所未有的吡喃-环己烯酮-二氢呋喃序列和六个立体中心以及两个手性轴,是第一个氧桥联二聚体萘基异喹啉生物碱。它们从一种尚未鉴定的刚果Ancistrocladus 物种的叶子中分离出来。它们的立体结构通过光谱、化学和旋光方法以及 DFT 和 TDDFT 计算相结合来确定。它们显然源自“开链”萘基异喹啉二聚体的级联氧化环化反应,并表现出显著的抗原生动物活性。

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