Tandem rh(I)-catalyzed [(5+2)+1] cycloaddition/aldol reaction for the construction of linear triquinane skeleton: Total syntheses of (+/-)-hirsutene and (+/-)-1-desoxyhypnophilin
文献类型：期刊论文
| 作者 | Jiao, Lei; Yuan, Changxia; Yu, Zhi-Xiang |
| 刊名 | journal of the american chemical society
 |
| 出版日期 | 2008-04-02 |
| 卷号 | 130期号:13页码:4421-4430 |
| 英文摘要 | a tandem reaction involving a rh(i)-catalyzed two-component [(5+2)+1] cycloaddition and an aldol condensation has been developed to construct the tricyclo[6.3.0.0(2,6)]undecane skeleton and its heteroatom-imbedded analogues. meanwhile, this method has been successfully applied to natural product synthesis for the first time. the present strategy enables a straightforward approach to the natural linear triquinane skeleton, as demonstrated by concise and step economical syntheses of hirsutene and 1-desoxyhypnophilin, whereby the linear triquinane core is diastereoselectively established in one manipulation with correct placement of all stereocenters, including two quarternary centers. this first application of the rh(i)-catalyzed [(5+2)+1] cycloaddition in natural product synthesis highlights the efficiency of this methodology for constructing complex fused ring systems. |
| WOS标题词 | science & technology ; physical sciences |
| 类目[WOS] | chemistry, multidisciplinary |
| 研究领域[WOS] | chemistry |
| 关键词[WOS] | catalyzed 5+2 cycloaddition ; asymmetric total-synthesis ; 3-component cycloadditions ; natural-products ; ideal synthesis ; hirsutene ; vinylcyclopropanes ; (&/-)-hirsutene ; rearrangement ; metathesis |
| 收录类别 | SCI ; IC ; CCR |
| 语种 | 英语 |
| WOS记录号 | WOS:000254549000043 |
| 公开日期 | 2015-11-17 |
| 源URL | [http://159.226.238.44/handle/321008/140754]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 作者单位 | Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Engn,Coll Chem, Beijing 100871, Peoples R China |
| 推荐引用方式 GB/T 7714 | Jiao, Lei,Yuan, Changxia,Yu, Zhi-Xiang. Tandem rh(I)-catalyzed [(5+2)+1] cycloaddition/aldol reaction for the construction of linear triquinane skeleton: Total syntheses of (+/-)-hirsutene and (+/-)-1-desoxyhypnophilin[J]. journal of the american chemical society,2008,130(13):4421-4430. |
| APA | Jiao, Lei,Yuan, Changxia,&Yu, Zhi-Xiang.(2008).Tandem rh(I)-catalyzed [(5+2)+1] cycloaddition/aldol reaction for the construction of linear triquinane skeleton: Total syntheses of (+/-)-hirsutene and (+/-)-1-desoxyhypnophilin.journal of the american chemical society,130(13),4421-4430. |
| MLA | Jiao, Lei,et al."Tandem rh(I)-catalyzed [(5+2)+1] cycloaddition/aldol reaction for the construction of linear triquinane skeleton: Total syntheses of (+/-)-hirsutene and (+/-)-1-desoxyhypnophilin".journal of the american chemical society 130.13(2008):4421-4430. |
入库方式： OAI收割
来源：大连化学物理研究所
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