Total synthesis of indole alkaloid (+/-)-subincanadine F via SmI2-mediated ring opening and bridge-forming Mannich reaction

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	Total synthesis of indole alkaloid (+/-)-subincanadine F via SmI2-mediated ring opening and bridge-forming Mannich reaction
	Gao P(高鹏) ; LIU YANQIN ; ZHANG LEI ; Xu PF(许鹏飞) ; WANG SHAOWU ; Lu Y(路勇) ; He MY(何鸣元) ; Zhai HB(翟宏斌)
刊名	J. Org. Chem.
	2006
卷号	71 期号:25 页码:9495-9498
ISSN号	0022-3263
其他题名	Total synthesis of indole alkaloid (+/-)-subincanadine F via SmI2-mediated ring opening and bridge-forming Mannich reaction
通讯作者	翟宏斌
英文摘要	The first total synthesis of (+/-)-subincanadine F, a bioactive indole alkaloid structurally featuring a 1-azabicyclo[4.3.1]-decane unit, has been realized from 1-(para-methoxybenzyl)-tryptamine in six steps. The bridge-containing tetracyclic framework of subincanadine F was efficiently assembled by a SmI2-mediated ring opening followed by an acid-mediated Mannich reaction. In addition, the tetracyclic ketoester 6, a key intermediate potentially useful for synthesizing structurally related indole alkaloids as well, was obtained in one step from alpha,beta-diketoester 5.
学科主题	天然产物有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jo061724h
语种	英语
WOS记录号	WOS:000242426900031
公开日期	2013-06-19
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/25585]
专题	上海有机化学研究所_中科院天然产物有机化学重点实验室
推荐引用方式 GB/T 7714	Gao P,LIU YANQIN,ZHANG LEI,et al. Total synthesis of indole alkaloid (+/-)-subincanadine F via SmI2-mediated ring opening and bridge-forming Mannich reaction[J]. J. Org. Chem.,2006,71(25):9495-9498.
APA	高鹏.,LIU YANQIN.,ZHANG LEI.,许鹏飞.,WANG SHAOWU.,...&翟宏斌.(2006).Total synthesis of indole alkaloid (+/-)-subincanadine F via SmI2-mediated ring opening and bridge-forming Mannich reaction.J. Org. Chem.,71(25),9495-9498.
MLA	高鹏,et al."Total synthesis of indole alkaloid (+/-)-subincanadine F via SmI2-mediated ring opening and bridge-forming Mannich reaction".J. Org. Chem. 71.25(2006):9495-9498.