Ir-Catalyzed Asymmetric Total Syntheses of Bisdehydrotuberostemonine D, Putative Bisdehydrotuberostemonine E and Structural Revision of the Latter

doi:10.1021/jacs.1c11265

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	Ir-Catalyzed Asymmetric Total Syntheses of Bisdehydrotuberostemonine D, Putative Bisdehydrotuberostemonine E and Structural Revision of the Latter
	Deng,Yi ; Liang,Xiao; Wei,Kun ; Yang,Yu-Rong
	2021
发表期刊	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN	0002-7863
卷号	143 期号:49 页码:20622-20627
摘要	The first total syntheses of bisdehydrotuberostemonine D (8) and putative bisdehydrotuberostemonine E (9), two novel pyrrole Stemona alkaloids, along with the synthesis of bisdehydrotuberostemonine (3) have been completed in 12-13 steps. Our strategy harnesses the power of transition-metal-catalyzed reactions employing Ir, Ru, and Pd, in particular Ir-catalyzed asymmetric allylation of aldehydes, two distinct protocols recently developed by Carreira and Krische, respectively. The threefold use of Ir catalysis, first in the stereodivergent construction of two contiguous stereocenters at C (9,10) and then in rapid formation of the two.-butyrolactone motifs, enabled the route's efficiency. Through this work, the originally assigned structure of bisdehydrotuberostemonine E (9) should be revised as 18a-bisdehydrotuberostemonine D (8*).
关键词	ENANTIOSELECTIVE TOTAL-SYNTHESIS ALDEHYDE OXIDATION LEVEL UNIFIED TOTAL-SYNTHESIS STEMONA ALKALOIDS CARBONYL ALLYLATION ALPHA-ALLYLATION IRIDIUM ALCOHOL TUBEROSTEMONINE HYDROGENATION
DOI	10.1021/jacs.1c11265
WOS记录号	WOS:000750799000053
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/73138
专题	中国科学院昆明植物研究所
作者单位	1.[Deng, Yi 2.Liang, Xiao 3.Wei, Kun 4.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources We, Kunming 650201, Yunnan, Peoples R China
推荐引用方式 GB/T 7714	Deng,Yi,Liang,Xiao,Wei,Kun,et al. Ir-Catalyzed Asymmetric Total Syntheses of Bisdehydrotuberostemonine D, Putative Bisdehydrotuberostemonine E and Structural Revision of the Latter[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2021,143(49):20622-20627.
APA	Deng,Yi,Liang,Xiao,Wei,Kun,&Yang,Yu-Rong.(2021).Ir-Catalyzed Asymmetric Total Syntheses of Bisdehydrotuberostemonine D, Putative Bisdehydrotuberostemonine E and Structural Revision of the Latter.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,143(49),20622-20627.
MLA	Deng,Yi,et al."Ir-Catalyzed Asymmetric Total Syntheses of Bisdehydrotuberostemonine D, Putative Bisdehydrotuberostemonine E and Structural Revision of the Latter".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 143.49(2021):20622-20627.

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