Catalytic Asymmetric Total Synthesis of (+)- and (-)-Paeoveitol via a Hetero-Diels-Alder Reaction

doi:10.1021/acs.orglett.6b03801

	Catalytic Asymmetric Total Synthesis of (+)- and (-)-Paeoveitol via a Hetero-Diels-Alder Reaction
	Li,Tian-Ze; Geng,Chang-An; Yin,Xiu-Juan; Yang,Tong-Hua; Chen,Xing-Long; Huang,Xiao-Yan; Ma,Yun-Bao; Zhang,Xue-Mei; Chen,Ji-Jun
	2017
发表期刊	ORGANIC LETTERS
ISSN	1523-7060
卷号	19 期号:3 页码:429-431
摘要	The first catalytic asymmetric total synthesis of (+)- and (-)-paeoveitol has been accomplished in 42% overall yield via a biomimetic hetero-Diels-Alder reaction. The chiral phosphoric acid catalyzed hetero-Diels-Alder reaction showed excellent diastereo- and enantioselectivity (>99:1 dr and 90% ee); two rings and three stereocenters were constructed in a single step to produce (-)-paeoveitol on a scale of 452 mg. This strategy enabled us to selectively synthesize both paeoveitol enantiomers from the same substrates by simply changing the enantiomer of the catalyst.
关键词	Ortho-quinone Methides Paeonia-veitchii Natural-products Paeoveitol
学科领域	Chemistry, Organic
DOI	10.1021/acs.orglett.6b03801
收录类别	SCI
语种	英语
引用统计	被引频次：32[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/54965
专题	植物化学与西部植物资源持续利用国家重点实验室
推荐引用方式 GB/T 7714	Li,Tian-Ze,Geng,Chang-An,Yin,Xiu-Juan,et al. Catalytic Asymmetric Total Synthesis of (+)- and (-)-Paeoveitol via a Hetero-Diels-Alder Reaction[J]. ORGANIC LETTERS,2017,19(3):429-431.
APA	Li,Tian-Ze.,Geng,Chang-An.,Yin,Xiu-Juan.,Yang,Tong-Hua.,Chen,Xing-Long.,...&Chen,Ji-Jun.(2017).Catalytic Asymmetric Total Synthesis of (+)- and (-)-Paeoveitol via a Hetero-Diels-Alder Reaction.ORGANIC LETTERS,19(3),429-431.
MLA	Li,Tian-Ze,et al."Catalytic Asymmetric Total Synthesis of (+)- and (-)-Paeoveitol via a Hetero-Diels-Alder Reaction".ORGANIC LETTERS 19.3(2017):429-431.

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