Asymmetric total synthesis of (−)-lingzhiol via a Rh-catalysed [3+2] cycloaddition
作者： Rong Long , Jun Huang , Wenbin Shao , Song Liu , Yu Lan
DOI: 10.1038/NCOMMS6707
关键词:
摘要: Bicyclic rings with quaternary bridgehead positions are difficult targets, yet frequently observed in nature. Here, the authors report a cycloaddition reaction giving access to these structures stereoselective manner and employ it as key step natural product total synthesis.
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Dominic M.T. Chan, Transition Metal Mediated Cycloadditions Reference Module in Chemistry, Molecular Sciences and Chemical Engineering#R##N#Comprehensive Organic Synthesis. ,vol. 3, pp. 271- 314 ,(1991) , 10.1016/B978-0-08-052349-1.00127-X
Paul Knochel, Gary A. Molander, Comprehensive organic synthesis Elsevier. ,(2014)
Vladimir B. Birman, Samuel J. Danishefsky, The total synthesis of (+/-)-merrilactone A. Journal of the American Chemical Society. ,vol. 124, pp. 2080- 2081 ,(2002) , 10.1021/JA012495D
John M. Hatcher, Don M. Coltart, Copper(I)-catalyzed addition of Grignard reagents to in situ-derived N-sulfonyl azoalkenes: an umpolung alkylation procedure applicable to the formation of up to three contiguous quaternary centers. Journal of the American Chemical Society. ,vol. 132, pp. 4546- 4547 ,(2010) , 10.1021/JA100932Q
Liao-Bin Dong, Xiu Gao, Fei Liu, Juan He, Xing-De Wu, Yan Li, Qin-Shi Zhao, None, Isopalhinine A, a unique pentacyclic Lycopodium alkaloid from Palhinhaea cernua. Organic Letters. ,vol. 15, pp. 3570- 3573 ,(2013) , 10.1021/OL401411M
Miyuki Kaneda, Rumiko Takahashi, Yoichi Iitaka, Shoji Shibata, Retigeranic acid, a novel sesterterpene isolated from the lichens of group Tetrahedron Letters. ,vol. 13, pp. 4609- 4611 ,(1972) , 10.1016/S0040-4039(01)94378-3
Arnaud Voituriez, Armen Panossian, Nicolas Fleury-Brégeot, Pascal Retailleau, Angela Marinetti, 2-Phospha[3]ferrocenophanes with planar chirality: synthesis and use in enantioselective organocatalytic [3 + 2] cyclizations. Journal of the American Chemical Society. ,vol. 130, pp. 14030- 14031 ,(2008) , 10.1021/JA806060A
Pinjing Zhao, Christopher D. Incarvito, John F. Hartwig, Carbon−Oxygen Bond Formation between a Terminal Alkoxo Ligand and a Coordinated Olefin. Evidence for Olefin Insertion into a Rhodium Alkoxide Journal of the American Chemical Society. ,vol. 128, pp. 9642- 9643 ,(2006) , 10.1021/JA063347W
Bryan J. Cowen, Scott J. Miller, Enantioselective [3 + 2]-Cycloadditions Catalyzed by a Protected, Multifunctional Phosphine-Containing α-Amino Acid Journal of the American Chemical Society. ,vol. 129, pp. 10988- 10989 ,(2007) , 10.1021/JA0734243
Yuan-Qing Fang, Eric N. Jacobsen, Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3 + 2] cycloadditions. Journal of the American Chemical Society. ,vol. 130, pp. 5660- 5661 ,(2008) , 10.1021/JA801344W