SmI2-Mediated intermolecular coupling of γ-lactam N-α-radicals with activated alkenes: Asymmetric synthesis of 11-hydroxylated analogues of the lead compounds CP-734432 and PF-04475270

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	SmI2-Mediated intermolecular coupling of γ-lactam N-α-radicals with activated alkenes: Asymmetric synthesis of 11-hydroxylated analogues of the lead compounds CP-734432 and PF-04475270
	Hu, Kong-Zhen ; Ma, Jie ; Qiu, Shi ; Zheng, Xiao ; Huang, Pei-Qiang ; Huang PQ(黄培强)
刊名	http://dx.doi.org/10.1021/jo301277n
	2013
关键词	Amides Hydroxylation Olefins
英文摘要	We report, for the first time, the synthesis of 8-aza-analogues of PGE 2. The SmI2-mediated cross coupling reactions of γ-lactam-hemiaminal 9, lactam 2-pyridyl sulfide 17, and lactam 2-pyridyl sulfone 18 with activated alkenes/alkyne were first developed, giving the corresponding γ-lactams in 49-78%, 45-75%, and 75-90%, respectively. The reactions of lactam 2-pyridyl sulfide and 2-pyridyl sulfone proceeded with ≥12:1 trans-diastereoselectivities. This represents the first intermolecular coupling reaction of the γ-lactam N-α-alkyl radicals of types B, B1, and B2 with activated alkenes. Two radical-based mechanisms were suggested. The asymmetric synthesis of the 11-hydroxylated analogue of the highly selective EP4 receptor agonist PF-04475270 (30), the 11-hydroxylated analogue of ocular hypotensive CP-734432 (31), compounds 35 and 36 have been achieved on the basis of this method. ? 2012 American Chemical Society.
语种	英语
出版者	American Chemical Society
内容类型	期刊论文
源URL	[http://dspace.xmu.edu.cn/handle/2288/89127]
专题	化学化工－已发表论文
推荐引用方式 GB/T 7714	Hu, Kong-Zhen,Ma, Jie,Qiu, Shi,et al. SmI2-Mediated intermolecular coupling of γ-lactam N-α-radicals with activated alkenes: Asymmetric synthesis of 11-hydroxylated analogues of the lead compounds CP-734432 and PF-04475270[J]. http://dx.doi.org/10.1021/jo301277n,2013.
APA	Hu, Kong-Zhen,Ma, Jie,Qiu, Shi,Zheng, Xiao,Huang, Pei-Qiang,&黄培强.(2013).SmI2-Mediated intermolecular coupling of γ-lactam N-α-radicals with activated alkenes: Asymmetric synthesis of 11-hydroxylated analogues of the lead compounds CP-734432 and PF-04475270.http://dx.doi.org/10.1021/jo301277n.
MLA	Hu, Kong-Zhen,et al."SmI2-Mediated intermolecular coupling of γ-lactam N-α-radicals with activated alkenes: Asymmetric synthesis of 11-hydroxylated analogues of the lead compounds CP-734432 and PF-04475270".http://dx.doi.org/10.1021/jo301277n (2013).