Communesin生物碱核心五环骨架的高效合成

doi:10.6023/cjoc202408006

研究论文

Communesin生物碱核心五环骨架的高效合成

杨之同^a, 宋恒谦^a, 雷盼^a, 闫嘉航^a,*, 谢卫青^a,b,*

^a西北农林科技大学化学与药学院陕西杨凌 712100;
^b陕西省植物源农药研究与开发重点实验室陕西杨凌 712100

收稿日期:2024-08-06 修回日期:2024-09-09
基金资助:
国家自然科学基金(No. 22301245 , 22371231 )资助项目.

Efficient Construction of the Core Pentacyclic Skeleton of Communesin Alkaloids

Zhitong Yang^a, Hengqian Song^a, Pan Lei^a, Jiahang Yan^a,*, Weiqing Xie^a,b,*

^aCollege of Chemistry & Pharmacy, Northwest A& F University, Yangling, Shaanxi 712100;
^bKey Laboratory of Botanical Pesticide R& D in Shaanxi Province, Yangling, Institution, Shaanxi 712100;

Received:2024-08-06 Revised:2024-09-09
Contact: * E-mail: xiewq@nwafu.edu.cn
Supported by:
National Natural Science Foundation of China (No. 22301245 , 22371231 )

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摘要/Abstract

Communesin生物碱是从海洋青霉属真菌中分离出来的一类复杂二聚环色胺生物碱,具有显著杀虫、抑制细胞增殖和细胞毒性. 结构上,这类天然产物有着独特的笼状七元稠环骨架,含有至少5个手性中心,其中2个为连续季碳中心,在合成上具有很大的挑战性. 本文报道了一种快速构建核心五环骨架的策略,关键步骤包括镍(II)/手性双氮氧配体催化的不对称共轭加成反应构建连续季碳中心以及串联脱保护/开环/关环反应构筑五环骨架.

关键词: communesin, 连续季碳, 不对称催化, 共轭加成, 串联环化

Communesin alkaloids are a family of complex dimeric cyclotryptamine alkaloids isolated from the marine fungi of the genus Penicillium. These indole alkaloids contain a unique caged heptacyclic skeleton along with five stereogenic centers at least, two of which are the contiguous quaternary carbon centers (CQCCs), thus presenting remarkable synthetic challenges. Herein, we develop an expedient construction the core pentacyclic ring system of communesins. The key steps include a catalytic asymmetric conjugated addition promoted by Ni(II)/chiral N,O-chiral dioxide for establishing the CQCCs and a deprotection/ring-opening reaction/cyclization cascade for setting up the pentacyclic skeleton.

Key words: communesin, contiguous quaternary carbon, asymmetric catalysis, conjugated addition, cascade cyclization

引用此文

杨之同, 宋恒谦, 雷盼, 闫嘉航, 谢卫青. Communesin生物碱核心五环骨架的高效合成[J]. 有机化学, doi: 10.6023/cjoc202408006.

Zhitong Yang, Hengqian Song, Pan Lei, Jiahang Yan, Weiqing Xie. Efficient Construction of the Core Pentacyclic Skeleton of Communesin Alkaloids[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202408006.

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