Divergent Total Synthesis of Triptolide, Triptonide, Tripdiolide, 16-Hydroxytriptolide, and Their Analogues

doi:10.1021/jo501744j

	Divergent Total Synthesis of Triptolide, Triptonide, Tripdiolide, 16-Hydroxytriptolide, and Their Analogues
	Xu, Hongtao; Tang, Huanyu; Feng, Huijin; Li, Yuanchao
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2014-11-07
卷号	79 期号:21 页码:10110-10122
ISSN号	0022-3263
DOI	10.1021/jo501744j
文献子类	Article
英文摘要	A divergent route was developed for the formal total synthesis of triptolide, triptonide, and tripdiolide, as well as a total synthesis of 16-hydroxytriptolide and their analogues in an enantioselective form. Common advanced intermediate 5 was concisely assembled by employing an indium(III)-catalyzed cationic polycyclization reaction and a palladium-catalyzed carbonylationlactone formation reaction as key steps. This advanced intermediate was readily converted to the above natural products by using palladium-catalyzed cross-coupling or the Claisen rearrangement reaction as key steps. Additionally, preliminary structurecytotoxic activity relationship studies of C13 suggested that it might be a new modification site that could still retain the cytotoxicity.
资助项目	National Natural Science Foundation of NFSC, China[81373479] ; Shanghai Science and Technology Commission "biomedicine technology support project", China[13431900403]
WOS关键词	ASYMMETRIC TRANSFER HYDROGENATION ; PALLADIUM-CATALYZED CARBONYLATION ; TRIPTERYGIUM-WILFORDII ; POLYENE CYCLIZATIONS ; KETONES ; ACID ; (-)-TRIPTOLIDE ; LACTONES ; ALCOHOLS ; DESIGN
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000344638200017
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276841]
专题	药物化学研究室
通讯作者	Li, Yuanchao
作者单位	Chinese Acad Sci, Shanghai Inst Mat Med, Dept Med Chem, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Xu, Hongtao,Tang, Huanyu,Feng, Huijin,et al. Divergent Total Synthesis of Triptolide, Triptonide, Tripdiolide, 16-Hydroxytriptolide, and Their Analogues[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(21):10110-10122.
APA	Xu, Hongtao,Tang, Huanyu,Feng, Huijin,&Li, Yuanchao.(2014).Divergent Total Synthesis of Triptolide, Triptonide, Tripdiolide, 16-Hydroxytriptolide, and Their Analogues.JOURNAL OF ORGANIC CHEMISTRY,79(21),10110-10122.
MLA	Xu, Hongtao,et al."Divergent Total Synthesis of Triptolide, Triptonide, Tripdiolide, 16-Hydroxytriptolide, and Their Analogues".JOURNAL OF ORGANIC CHEMISTRY 79.21(2014):10110-10122.