ICCAS OpenIR
Formal syntheses of (+/-)-Asterisca-3(15),6-diene and (+/-)-Pentalenene using Rh(I)-catalyzed [(5+2)+1] cycloaddition
Fan, Xiaohui1,2,3; Zhuo, Lian-Gang1; Tu, Yong Qiang2,3; Yu, Zhi-Xiang1
2009-06-13
Source PublicationTETRAHEDRON
ISSN0040-4020
Volume65Issue:24Pages:4709-4713
AbstractEfficient formal syntheses of (+/-)-Asterisca-3(15),6-diene, a natural product with a bicyclo[6.3.0]undecane skeleton, and (+/-)-Pentalenene. a natural product with a tricyclo[6.3.0.0(4,8)]undecane skeleton, have been achieved by using Rh(I)-catalyzed [(5+2)+1] cycloaddition. The [(5+2)+1] reaction provides an expeditious approach to reach the bicyclic cyclooctenone 4, which was quickly transformed (via hydroboration then oxidation) to diketone 14, a key advanced intermediate for the total synthesis of (+/-)-Asterisca-3(15),6-diene. Through further transformations, 14 was converted to diene 18, an advanced intermediate for the total synthesis of (+/-)-Pentalenene. (C) 2009 Elsevier Ltd. All rights reserved.
DOI10.1016/j.tet.2009.04.020
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000266751900011
PublisherPERGAMON-ELSEVIER SCIENCE LTD
Citation statistics
Cited Times:32[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/67632
Collection中国科学院化学研究所
Corresponding AuthorYu, Zhi-Xiang
Affiliation1.Peking Univ, BNLMS, Minist Educ, Key Lab Bioorgan Chem & Mol Engn,Coll Chem, Beijing 100871, PR, Peoples R China
2.Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
3.Lanzhou Univ, Dept Chem, Lanzhou 730000, Peoples R China
Recommended Citation
GB/T 7714
Fan, Xiaohui,Zhuo, Lian-Gang,Tu, Yong Qiang,et al. Formal syntheses of (+/-)-Asterisca-3(15),6-diene and (+/-)-Pentalenene using Rh(I)-catalyzed [(5+2)+1] cycloaddition[J]. TETRAHEDRON,2009,65(24):4709-4713.
APA Fan, Xiaohui,Zhuo, Lian-Gang,Tu, Yong Qiang,&Yu, Zhi-Xiang.(2009).Formal syntheses of (+/-)-Asterisca-3(15),6-diene and (+/-)-Pentalenene using Rh(I)-catalyzed [(5+2)+1] cycloaddition.TETRAHEDRON,65(24),4709-4713.
MLA Fan, Xiaohui,et al."Formal syntheses of (+/-)-Asterisca-3(15),6-diene and (+/-)-Pentalenene using Rh(I)-catalyzed [(5+2)+1] cycloaddition".TETRAHEDRON 65.24(2009):4709-4713.
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