Cheng Min-Jing, Cao Jia-Qing, Yang Xin-Yi, Zhong Li-Ping, Hu Li-Jun, Lu Xi, Hou Bao-Long, Hu Ya-Jian, Wang Ying, You Xue-Fu, Wang Lei, Ye Wen-Cai, Li Chuang-Chuang
College of Pharmacy , Jinan University , Guangzhou 510632 , China . Email:
Department of Chemistry , Southern University of Science and Technology , Shenzhen 518055 , China . Email:
Chem Sci. 2017 Nov 27;9(6):1488-1495. doi: 10.1039/c7sc04672c. eCollection 2018 Feb 14.
Herein, we describe a concise catalytic approach to the first asymmetric total syntheses of myrtucommuacetalone, myrtucommuacetalone B, and callistrilones A, C, D and E. The syntheses proceed in only 5-7 steps from the readily available compound , without the need for protecting groups. Key features of the syntheses include a unique organocatalytic asymmetric Friedel-Crafts-type Michael addition with high enantioselectivity and a broad substrate scope, a novel Michael-ketalization-annulation cascade reaction, and an oxidative [3 + 2] cycloaddition. Furthermore, the new compound exhibited potent antibacterial activities against several multidrug-resistant strains (MRSA, VISA and VRE), and showed greater potency than vancomycin.
在此，我们描述了一种简洁的催化方法，用于首次不对称全合成桃金娘酮、桃金娘酮B以及卡里斯特里酮A、C、D和E。这些合成仅从容易获得的化合物开始，经过5至7步反应即可完成，无需使用保护基团。合成的关键特征包括具有高对映选择性和广泛底物范围的独特有机催化不对称傅克型迈克尔加成、新颖的迈克尔-缩酮化-环化串联反应以及氧化[3+2]环加成。此外，新化合物对几种耐多药菌株（耐甲氧西林金黄色葡萄球菌、万古霉素中度敏感金黄色葡萄球菌和耐万古霉素肠球菌）表现出强效抗菌活性，且显示出比万古霉素更强的效力。
