Towards Stereochemical Control: Two Approaches for the Highly anti-Diastereoselective Construction of the Spirolactone Moieties of Some Stemona Alkaloids

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	Towards Stereochemical Control: Two Approaches for the Highly anti-Diastereoselective Construction of the Spirolactone Moieties of Some Stemona Alkaloids
	Tuo, Shichuan ; Liu, Xuekui ; Huang, Peiqiang ; Huang PQ(黄培强)
刊名	http://dx.doi.org/10.1002/cjoc.201200904
	2013-01
英文摘要	Some Stemona alkaloids belonging to the tuberostemospironine group possess a spirolactone moiety with anti-configuration (C-9/C-9a). In this paper, we describe two approaches to this structural unity. By using bromine atom as a traceless directing group, the SmI2-mediated reductive coupling of ketone 6 and β-bromomethacrylate proceeded with complete anti-diastereoselectivity. In the absence of an α-directing (chelation) group, the one-pot reaction of the ketone derived from alcohol 15 with the organozinc reagent generated from bromomethacrylate afforded spiro-α-methylene-γ-lactone derivative 16 as a single diastereomer. These two highly diastereoselective methods would find application in the synthesis of stemona alkaloids containing anti-configured spiro-lactone/pyrrolidine moieties. In addition, on the basis of our previous work, the total synthesis of (−)-9-epi-11-demethylsessilifoliamide J (11), and an improved synthesis of (−)-9,11-di-epi-sessilifoliamide J were accomplished.Completely anti-diastereoselective: This can be achieved by using bromine atom as a traceless directing group in the SmI2-mediated reductive coupling of α,β-unsaturated ester with ketones; or by the one-pot reaction of the organozinc reagent generated from bromomethacrylate with ketone. On the basis of these results, two approaches to the spirolactone moiety with anti-configuration (C-9/C-9a) found in some Stemona alkaloids were disclosed.
语种	英语
内容类型	期刊论文
源URL	[http://dspace.xmu.edu.cn/handle/2288/64439]
专题	化学化工－已发表论文
推荐引用方式 GB/T 7714	Tuo, Shichuan,Liu, Xuekui,Huang, Peiqiang,et al. Towards Stereochemical Control: Two Approaches for the Highly anti-Diastereoselective Construction of the Spirolactone Moieties of Some Stemona Alkaloids[J]. http://dx.doi.org/10.1002/cjoc.201200904,2013.
APA	Tuo, Shichuan,Liu, Xuekui,Huang, Peiqiang,&黄培强.(2013).Towards Stereochemical Control: Two Approaches for the Highly anti-Diastereoselective Construction of the Spirolactone Moieties of Some Stemona Alkaloids.http://dx.doi.org/10.1002/cjoc.201200904.
MLA	Tuo, Shichuan,et al."Towards Stereochemical Control: Two Approaches for the Highly anti-Diastereoselective Construction of the Spirolactone Moieties of Some Stemona Alkaloids".http://dx.doi.org/10.1002/cjoc.201200904 (2013).