Catalytic asymmetric total syntheses of myrtucommuacetalone, myrtucommuacetalone B, and callistrilones A, C, D and E

Autor:	Chuang-Chuang Li, Lei Wang, Jia-Qing Cao, Xi Lu, Ya-Jian Hu, Wen-Cai Ye, Ying Wang, Xinyi Yang, Min-Jing Cheng, Li-Ping Zhong, Hu Lijun, Xuefu You, Bao-Long Hou
Rok vydání:	2018
Předmět:	010405 organic chemistry Chemistry Stereochemistry Substrate (chemistry) General Chemistry 010402 general chemistry Key features 01 natural sciences Combinatorial chemistry Cycloaddition 0104 chemical sciences Catalysis Cascade reaction Michael reaction
Zdroj:	Chemical Science. 9:1488-1495
ISSN:	2041-6539 2041-6520
DOI:	10.1039/c7sc04672c
Popis:	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 11, 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 7 exhibited potent antibacterial activities against several multidrug-resistant strains (MRSA, VISA and VRE), and showed greater potency than vancomycin.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9f0d27e648b84c6b69f39713d13a426c https://doi.org/10.1039/c7sc04672c Zobrazit plný text záznamu