Enantioselective Total Synthesis of (-)-Daphenylline

doi:10.1021/jacs.3c12741

KIB OpenIR

	Enantioselective Total Synthesis of (-)-Daphenylline
	Wu, Bing-Lu; Yao, Jian-Neng; Long, Xiang-Xi; Tan, Zong-Qin; Liang, Xiao; Feng, Li; Wei, Kun; Yang, Yu-Rong
	2024
发表期刊	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN	0002-7863
卷号	146 期号:2 页码:1262-1268
摘要	A concise enantioselective total synthesis of (-)-daphenylline, a hexacyclic Daphniphyllum alkaloid with a unique benzene ring, was achieved in 14 steps. The synthesis commences with two chiral stereocenters, C2 and C18, readily installed via Carreira's Ir/amine dual-catalyzed allylation. The allylic bridgehead amine 6 was rapidly prepared through Wickens' photoredox-catalyzed hydrocarboxylation of olefin and CuBr2-catalyzed alpha-amination of ketone. The tetracycle 4 was formed via Pd-catalyzed reductive Heck reaction or, more concisely, by Krische's Rh-catalyzed reductive 1,6-enyne cyclization. In this synthesis, newly reported Wickens' photoredox-catalyzed hydrocarboxylation was used twice, and Friedel-Crafts acylation thrice.
DOI	10.1021/jacs.3c12741
WOS记录号	WOS:001144599800001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/76240
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Wu, Bing-Lu,Yao, Jian-Neng,Long, Xiang-Xi,et al. Enantioselective Total Synthesis of (-)-Daphenylline[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2024,146(2):1262-1268.
APA	Wu, Bing-Lu.,Yao, Jian-Neng.,Long, Xiang-Xi.,Tan, Zong-Qin.,Liang, Xiao.,...&Yang, Yu-Rong.(2024).Enantioselective Total Synthesis of (-)-Daphenylline.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,146(2),1262-1268.
MLA	Wu, Bing-Lu,et al."Enantioselective Total Synthesis of (-)-Daphenylline".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 146.2(2024):1262-1268.

条目包含的文件		下载所有文件
文件名称/大小	文献类型	版本类型	开放类型	使用许可
10.1021_jacs.3c12741（2389KB）	期刊论文	出版稿	开放获取	CC BY-NC-SA	浏览下载