Ir-Catalyzed Asymmetric Total Syntheses of Bisdehydrotuberostemonine D, Putative Bisdehydrotuberostemonine E and Structural Revision of the Latter
文献类型：期刊论文
| 作者 | Deng,Yi; Liang,Xiao ; Wei,Kun; Yang,Yu-Rong
|
| 刊名 | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
 |
| 出版日期 | 2021 |
| 卷号 | 143期号:49页码:20622-20627 |
| 关键词 | ENANTIOSELECTIVE TOTAL-SYNTHESIS ALDEHYDE OXIDATION LEVEL UNIFIED TOTAL-SYNTHESIS STEMONA ALKALOIDS CARBONYL ALLYLATION ALPHA-ALLYLATION IRIDIUM ALCOHOL TUBEROSTEMONINE HYDROGENATION |
| ISSN号 | 0002-7863 |
| DOI | 10.1021/jacs.1c11265 |
| 英文摘要 | 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*). |
| WOS记录号 | WOS:000750799000053 |
| 源URL | [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.Liang, Xiao 2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources We, Kunming 650201, Yunnan, Peoples R China 3.[Deng, Yi 4.Wei, Kun |
| 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. |
入库方式： OAI收割
来源：昆明植物研究所
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