SmI2-Mediated Intermolecular Coupling of gamma-Lactam N-alpha-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 gamma-Lactam N-alpha-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 ; Zheng X(郑啸) ; Huang PQ(黄培强)
刊名	http://dx.doi.org/10.1021/jo301277n
	2013
关键词	TERT-BUTANESULFINYL IMINES EP4 RECEPTOR AGONISTS GLYCOSYL SAMARIUM(III) COMPOUNDS DIELS-ALDER REACTIONS D/E RING FUSION C-2-SYMMETRIC BIPYRROLIDINES ENANTIOSELECTIVE ADDITION STEREOSELECTIVE-SYNTHESIS ALLYLIC TRICHLOROSILANES INDOLIZIDINE ALKALOI
英文摘要	National Basic Research Program (973 Program) of China [2010CB833200]; NSF of China [21072160, 20832005]; We report, for the first time, the synthesis of 8-aza-analogues of PGE(2). The SmI2-mediated cross coupling reactions of gamma-lactam-hemiaminal 9, lactam 2-pyridyl sulfide 17, and lactam 2-pyridyl sulfone 18 with activated alkenes/allcyne were first developed, giving the corresponding gamma-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 gamma-lactam N-alpha-alkyl radicals of types B, 131, 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.
语种	英语
出版者	AMER CHEMICAL SOC
内容类型	期刊论文
源URL	[http://dspace.xmu.edu.cn/handle/2288/93389]
专题	医学院－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 gamma-Lactam N-alpha-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 gamma-Lactam N-alpha-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 gamma-Lactam N-alpha-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).