Divergent Total Syntheses of (-)-Huperzine Q, (+)-Lycopladine B,   (+)-Lycopladine C, and (-)-4-epi-Lycopladine D

doi:10.1002/asia.201700364

CORC > 北京大学 > 化学与分子工程学院

	Divergent Total Syntheses of (-)-Huperzine Q, (+)-Lycopladine B, (+)-Lycopladine C, and (-)-4-epi-Lycopladine D
	Hong, Benke ; Hu, Dachao ; Wu, Jinbao ; Zhang, Jing ; Li, Houhua ; Pan, Yingming ; Lei, Xiaoguang
刊名	CHEMISTRY-AN ASIAN JOURNAL
	2017
关键词	aldol reaction alkaloids metathesis natural products total synthesis CARBONYL-OLEFIN METATHESIS LYCOPODIUM ALKALOIDS FUNCTIONAL-GROUP ENOL ETHERS OXIDATION EPOXYAMINES KETONES (+)-FAWCETTIDINE REARRANGEMENT FAWCETTIMINE
DOI	10.1002/asia.201700364
英文摘要	We report herein our synthetic efforts towards the divergent syntheses of (-)-huperzine Q (1), (+)-lycopladine B (2), (+)-lycopladine C (3), and (-)-lycopladine D (4). The 10-step total synthesis of (-)-huperzine Q (1) and the first total syntheses of (+)-lycopladines B (2) and C (3) were accomplished through a series of cascade reactions. Our approach involved a Michael addition/aldol/intramolecular C-alkylation sequence to forge the 6/9 spirocycle ring, and this was followed by an ethylene-accelerated carbonyl-olefin metathesis to construct the common 6/5/9 ring system. Finally, latestage enamine bromofunctionalization enabled us to access (-)-huperzine Q (1), (+)-lycopladine B (2), and (+)-lycopladine C (3), and a tandem C4-epimerization/retro-Claisen condensation furnished (-)-4-epi-lycopladine D (63).; National Natural Science Foundation of China (NNSFC) [21625201, 21561142002, 21472010]; National High Technology Projects 973 [2015CB856200]; SCI(E); ARTICLE; 13,SI; 1557-1567; 12
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/472262]
专题	化学与分子工程学院生命科学学院
推荐引用方式 GB/T 7714	Hong, Benke,Hu, Dachao,Wu, Jinbao,et al. Divergent Total Syntheses of (-)-Huperzine Q, (+)-Lycopladine B, (+)-Lycopladine C, and (-)-4-epi-Lycopladine D[J]. CHEMISTRY-AN ASIAN JOURNAL,2017.
APA	Hong, Benke.,Hu, Dachao.,Wu, Jinbao.,Zhang, Jing.,Li, Houhua.,...&Lei, Xiaoguang.(2017).Divergent Total Syntheses of (-)-Huperzine Q, (+)-Lycopladine B, (+)-Lycopladine C, and (-)-4-epi-Lycopladine D.CHEMISTRY-AN ASIAN JOURNAL.
MLA	Hong, Benke,et al."Divergent Total Syntheses of (-)-Huperzine Q, (+)-Lycopladine B, (+)-Lycopladine C, and (-)-4-epi-Lycopladine D".CHEMISTRY-AN ASIAN JOURNAL (2017).