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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 ; Huang PQ(黄培强)
	2012-03-05
关键词	biosynthetic pathways computational chemistry natural products structure elucidation total synthesis
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 DessMartin 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.; National Basic Research Program (973 Program) of China [2010CB833200]; NSF of China [20832005, 21072160]; NFFTBS [J1030415]; NSF of Fujian Province of China [2011J01056]
语种	英语
出版者	WILEY-V C H VERLAG GMBH
内容类型	期刊论文
源URL	[http://dx.doi.org/10.1002/asia.201100809]
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],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..
MLA	Chen, Gui-Yang,et al."Enantioselective Syntheses of Rigidiusculamides A and B: Revision of the Relative Stereochemistry of Rigidiusculamide A".(2012).

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