A novel and versatile method for the enantioselective syntheses of tropane alkaloids

CORC > 厦门大学 > 化学化工－已发表论文

	A novel and versatile method for the enantioselective syntheses of tropane alkaloids
	Mao ZhongYi ; Huang SuYu ; Gao LongHui ; Wang AiE ; Huang PeiQiang ; Wang AE(王爱娥) ; Huang PQ(黄培强)
刊名	http://dx.doi.org/10.1007/s11426-013-4998-2
	2014
关键词	N-ACYLIMINIUM IONS INTERMOLECULAR ADDITION-REACTIONS VIBRATIONAL CIRCULAR-DICHROISM ASYMMETRIC TOTAL-SYNTHESIS COCAINE C-1 ANALOGS ABSOLUTE-CONFIGURATION DIRECT TRANSFORMATION REDUCTIVE ALKYLATION MULTIDRUG-RESISTANCE RADICAL CYCLIZATION
英文摘要	National Basic Research Program of China (973 Program) [2010CB833200]; National Natural Science Foundation of China [21072160, 21332007]; Program for Changjiang Scholars and Innovative Research Team at the University of the MOE; A full account of the novel and flexible approach to hydroxylated 8-azabicyclo[3,2,1]octan-3-ones and 9-azabicyclo[3,3,1] nonan-3-ones is presented. Using keto-lactams as the starting materials, this two-step method consists of silyl enol ether formation with TBDMSOTf, lactam activation with Tf2O/DTBMP, and halide-promoted cyclization. Radical dechlorination of the resulting 1-halotropan-3-ones led to the corresponding hydroxylated tropan-3-ones, which can be hydrogenated to yield 3 alpha,6 beta-dihydroxytropanes. Starting from optically active keto-lactams, the method has been applied to the enantioselective syntheses of (+)-(1S,3S,5R,65)-pervilleine C (6), (+)-(1S,3R,5S,6R)-valeroidine (3), (+)-(1S,3S,5R,6,9)-dibenzoyloxytropane (8), and (+)-(1S,3S,5R,6S)-merredissine (9).
语种	英语
出版者	SCIENCE PRESS
内容类型	期刊论文
源URL	[http://dspace.xmu.edu.cn/handle/2288/89405]
专题	化学化工－已发表论文
推荐引用方式 GB/T 7714	Mao ZhongYi,Huang SuYu,Gao LongHui,et al. A novel and versatile method for the enantioselective syntheses of tropane alkaloids[J]. http://dx.doi.org/10.1007/s11426-013-4998-2,2014.
APA	Mao ZhongYi.,Huang SuYu.,Gao LongHui.,Wang AiE.,Huang PeiQiang.,...&黄培强.(2014).A novel and versatile method for the enantioselective syntheses of tropane alkaloids.http://dx.doi.org/10.1007/s11426-013-4998-2.
MLA	Mao ZhongYi,et al."A novel and versatile method for the enantioselective syntheses of tropane alkaloids".http://dx.doi.org/10.1007/s11426-013-4998-2 (2014).