Marine furanocembranoids-inspired macrocycles enabled by Pd-catalyzed unactivated C(sp(3))-H olefination mediated by donor/donor carbenes

doi:10.1038/s41467-021-21484-x

	Marine furanocembranoids-inspired macrocycles enabled by Pd-catalyzed unactivated C(sp(3))-H olefination mediated by donor/donor carbenes
	Hao, Jiping 1; Guo, Xueying 4; He, Shijun 1,3; Xu, Zhongliang 1; Chen, Lu 1; Li, Zhongyu 1; Song, Bichao 1; Zuo, Jianping 1,3; Lin, Zhenyang 4; Yang, Weibo 1,2,3
刊名	NATURE COMMUNICATIONS
	2021-02-26
卷号	12 期号:1 页码:11
ISSN号	2041-1723
DOI	10.1038/s41467-021-21484-x
通讯作者	Lin, Zhenyang(chzlin@ust.hk) ; Yang, Weibo(yweibo@simm.ac.cn)
英文摘要	Biomimetic modularization and function-oriented synthesis of structurally diversified natural product-like macrocycles in a step-economical fashion is highly desirable. Inspired by marine furanocembranoids, herein, we synthesize diverse alkenes substituted furan-embedded macrolactams via a modular biomimetic assembly strategy. The success of this assembly is the development of crucial Pd-catalyzed carbene coupling between ene-yne-ketones as donor/donor carbene precursors and unactivated Csp(3)H bonds which represents a great challenge in organic synthesis. Notably, this method not only obviates the use of unstable, explosive, and toxic diazo compounds, but also can be amenable to allenyl ketones carbene precursors. DFT calculations demonstrate that a formal 1,4-Pd shift could be involved in the mechanism. Moreover, the collected furanocembranoids-like macrolactams show significant anti-inflammatory activities against TNF-alpha, IL-6, and IL-1 beta and the cytotoxicity is comparable to Dexamethasone.
资助项目	100 talent program of Chinese Academy of Sciences, NSFC[21702217] ; 1000-Youth Talents Plan, Shanghai-Youth Talent, National Science & Technology Major Project Key New Drug Creation and Manufacturing Program China[2018ZX09711002-006] ; Science and Technology Commission of Shanghai Municipality[18431907100] ; Shanghai-Technology Innovation Action Plan[18JC1415300] ; Research Grants Council of Hong Kong[HKUST 16302418]
WOS研究方向	Science & Technology - Other Topics
语种	英语
出版者	NATURE RESEARCH
WOS记录号	WOS:000624978300015
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/295369]
专题	中国科学院上海药物研究所
通讯作者	Lin, Zhenyang; Yang, Weibo
作者单位	1.Chinese Acad Sci, Key Lab Receptor Res, Shanghai Inst Mat Med SIMM, Shanghai, Peoples R China 2.Univ Chinese Acad Sci, Sch Pharmaceut Sci & Technol, Hangzhou Inst Adv Study, Hangzhou, Peoples R China 3.Univ Chinese Acad Sci, Beijing, Peoples R China 4.Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
推荐引用方式 GB/T 7714	Hao, Jiping,Guo, Xueying,He, Shijun,et al. Marine furanocembranoids-inspired macrocycles enabled by Pd-catalyzed unactivated C(sp(3))-H olefination mediated by donor/donor carbenes[J]. NATURE COMMUNICATIONS,2021,12(1):11.
APA	Hao, Jiping.,Guo, Xueying.,He, Shijun.,Xu, Zhongliang.,Chen, Lu.,...&Yang, Weibo.(2021).Marine furanocembranoids-inspired macrocycles enabled by Pd-catalyzed unactivated C(sp(3))-H olefination mediated by donor/donor carbenes.NATURE COMMUNICATIONS,12(1),11.
MLA	Hao, Jiping,et al."Marine furanocembranoids-inspired macrocycles enabled by Pd-catalyzed unactivated C(sp(3))-H olefination mediated by donor/donor carbenes".NATURE COMMUNICATIONS 12.1(2021):11.