Total Synthesis of (+/-)-Cafestol: A Late-Stage Construction of the Furan Ring Inspired by a Biosynthesis Strategy

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	Total Synthesis of (+/-)-Cafestol: A Late-Stage Construction of the Furan Ring Inspired by a Biosynthesis Strategy
	Zhu LL(朱莉莉); Luo JS(罗济生); Hong R(洪然)
刊名	Org. Lett.
	2014
卷号	16 期号:8 页码:2162-2165
其他题名	Total Synthesis of (+/-)-Cafestol: A Late-Stage Construction of the Furan Ring Inspired by a Biosynthesis Strategy
通讯作者	洪然
英文摘要	An efficient bioinspired approach to the total synthesis of (+/-)-cafestol features a late-stage installation of the furan ring with a mild Au-catalyzed cycloisomerization. The Et2AlCl-promoted aldehyde-ene cyclization and subsequent Friedel Crafts reaction deliver a requisite tricyclic system in gram scale with high stereo- and regioselectivity. Moreover, a highly stereoselective SmI(2)mediated aldehyde alkene radical cyclization furnishes the key bicyclo[3.2.1]octane skeleton to offer an advanced intermediate for the synthesis of other oxygenated ent-kaurene diterpenoids.
学科主题	天然产物有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/ol500623w
语种	英语
内容类型	期刊论文
源URL	[http://ir.sioc.ac.cn/handle/331003/38979]
专题	上海有机化学研究所_中科院天然产物有机化学重点实验室
作者单位	中科院上海有机化学研究所
推荐引用方式 GB/T 7714	Zhu LL,Luo JS,Hong R. Total Synthesis of (+/-)-Cafestol: A Late-Stage Construction of the Furan Ring Inspired by a Biosynthesis Strategy[J]. Org. Lett.,2014,16(8):2162-2165.
APA	朱莉莉,罗济生,&洪然.(2014).Total Synthesis of (+/-)-Cafestol: A Late-Stage Construction of the Furan Ring Inspired by a Biosynthesis Strategy.Org. Lett.,16(8),2162-2165.
MLA	朱莉莉,et al."Total Synthesis of (+/-)-Cafestol: A Late-Stage Construction of the Furan Ring Inspired by a Biosynthesis Strategy".Org. Lett. 16.8(2014):2162-2165.