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Total Synthesis of (+/-)-Cafestol: A Late-Stage Construction of the Furan Ring Inspired by a Biosynthesis Strategy
Alternative TitleTotal 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)
2014
Source PublicationOrg. Lett.
Volume16Issue:8Pages:2162-2165
AbstractAn 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.
Subject Area天然产物有机化学
DOI10.1021/ol500623w
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Indexed BySCI
Language英语
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Cited Times:31[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/38979
Collection中科院天然产物有机化学重点实验室
Corresponding AuthorHong R(洪然)
Affiliation中科院上海有机化学研究所
Recommended Citation
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.
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