Enantioselective syntheses of rigidiusculamides A and B: Revision of the relative stereochemistry of rigidiusculamide A

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	Enantioselective syntheses of rigidiusculamides A and B: Revision of the relative stereochemistry of rigidiusculamide A
	Chen, Gui-Yang ; Huang, Huang ; Ye, Jian-Liang ; Wang, Ai-E ; Huang, Hui-Ying ; Zhang, Hong-Kui ; Huang, Pei-Qiang ; Wang AE(王爱娥) ; Zhang HK(张洪奎) ; Huang PQ(黄培强)
刊名	http://dx.doi.org/10.1002/asia.201100809
	2012-03-05
关键词	Computational chemistry Reaction intermediates Stereochemistry Stereoselectivity
英文摘要	The first enantioselective synthesis of cytotoxic natural products rigidiusculamides A (ent-21) and B (8) has been achieved by two synthetic routes. The first one is convergent based on the common intermediate 11, obtained through a high yielding SmI2-mediated Reformatsky-type reaction. A highly diastereoselective one-pot Dess-Martin periodinane-mediated bis-oxidation allowed the direct conversion of the diastereomeric mixture of 11 into rigidiusculamide B (8). Isolation of minor diastereomer 21, in combination with computational work, allowed us to suggest the structure of the natural rigidiusculamide A to be ent-21, as synthesized by the second route. Four diastereomers (7, ent-7, 22 a, and 22 b) and an enantiomer (21) of rigidiusculamide A (ent-21) have been synthesized. On the basis of literature precedents and computational work, a biosynthetic pathway for rigidiusculamides A and B was proposed to account for the opposite configuration at C-5 of those two congeners. 漏 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
语种	英语
出版者	John Wiley and Sons Ltd
内容类型	期刊论文
源URL	[http://dspace.xmu.edu.cn/handle/2288/89530]
专题	化学化工－已发表论文
推荐引用方式 GB/T 7714	Chen, Gui-Yang,Huang, Huang,Ye, Jian-Liang,et al. Enantioselective syntheses of rigidiusculamides A and B: Revision of the relative stereochemistry of rigidiusculamide A[J]. http://dx.doi.org/10.1002/asia.201100809,2012.
APA	Chen, Gui-Yang.,Huang, Huang.,Ye, Jian-Liang.,Wang, Ai-E.,Huang, Hui-Ying.,...&黄培强.(2012).Enantioselective syntheses of rigidiusculamides A and B: Revision of the relative stereochemistry of rigidiusculamide A.http://dx.doi.org/10.1002/asia.201100809.
MLA	Chen, Gui-Yang,et al."Enantioselective syntheses of rigidiusculamides A and B: Revision of the relative stereochemistry of rigidiusculamide A".http://dx.doi.org/10.1002/asia.201100809 (2012).