Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes via a gold-catalysed cascade reaction.

作者: Junkai Fu , Yueqing Gu , Hao Yuan , Tuoping Luo , Song Liu

DOI: 10.1038/NCOMMS9617

关键词:

摘要: The development of an efficient diastereoselective synthesis the oxabicyclo[3.2.1]octane ring system bearing two oxygenated quaternary chiral centres represents a significant challenge. This motif can be found in wide range natural products with biological activities. Here we report such kind scaffold using cyclohexane-trans-1,4-diol alkyne side chain presence Au(I) catalyst. is domino process which C–H, C–O and one C–C bond assembled through sequence cyclization/semi-pinacol rearrangements. strategy has been successfully applied to asymmetric formal total (+)-cortistatins.

参考文章(69)
Shinji Kitagaki, Masahiro Anada, Osamu Kataoka, Kentaro Matsuno, Chisato Umeda, Nobuhide Watanabe, Shun-ichi Hashimoto, Enantiocontrol in Tandem Carbonyl Ylide Formation and Intermolecular 1,3-Dipolar Cycloaddition of α-Diazo Ketones Mediated by Chiral Dirhodium(II) Carboxylate Catalyst Journal of the American Chemical Society. ,vol. 121, pp. 1417- 1418 ,(1999) , 10.1021/JA983748E
Matthias Rudolph, A. Stephen K. Hashmi, Gold catalysis in total synthesis—an update Chemical Society Reviews. ,vol. 41, pp. 2448- 2462 ,(2012) , 10.1039/C1CS15279C
Ranjala Ratnayake, David Covell, Tanya T. Ransom, Kirk R. Gustafson, John A. Beutler, Englerin A, a selective inhibitor of renal cancer cell growth, from Phyllanthus engleri. Organic Letters. ,vol. 11, pp. 57- 60 ,(2009) , 10.1021/OL802339W
Mei Xu, Tian-Tian Ren, Chuan-Ying Li, Gold-Catalyzed Oxidative Rearrangement of Homopropargylic Ether via Oxonium Ylide Organic Letters. ,vol. 14, pp. 4902- 4905 ,(2012) , 10.1021/OL302238T
Ross A. Widenhoefer, Feijie Song, Gold-Catalyzed Addition of Oxygen Nucleophiles to CC Multiple Bonds Catalyzed Carbon-Heteroatom Bond Formation. ,vol. 42, pp. 463- 492 ,(2010) , 10.1002/9783527633388.CH12
Ryan A. Shenvi, Carlos A. Guerrero, Jun Shi, Chuang-Chuang Li, Phil S. Baran, Synthesis of (+)-cortistatin A. Journal of the American Chemical Society. ,vol. 130, pp. 7241- 7243 ,(2008) , 10.1021/JA8023466
Alison R. Hardin Narayan, Eric M. Simmons, Richmond Sarpong, Synthetic Strategies Directed Towards the Cortistatin Family of Natural Products European Journal of Organic Chemistry. ,vol. 2010, pp. 3553- 3567 ,(2010) , 10.1002/EJOC.201000247
K. C. Nicolaou, Xiao-Shui Peng, Ya-Ping Sun, Damien Polet, Bin Zou, Chek Shik Lim, David Y.-K. Chen, Total synthesis and biological evaluation of cortistatins A and J and analogues thereof. Journal of the American Chemical Society. ,vol. 131, pp. 10587- 10597 ,(2009) , 10.1021/JA902939T
Tao Wang, Shuai Shi, Max M. Hansmann, Eva Rettenmeier, Matthias Rudolph, A. Stephen K. Hashmi, Synthesis of highly substituted 3-formylfurans by a gold(I)-catalyzed oxidation/1,2-alkynyl migration/cyclization cascade. Angewandte Chemie. ,vol. 53, pp. 3715- 3719 ,(2014) , 10.1002/ANIE.201310146
Tao Wang, Long Huang, Shuai Shi, Matthias Rudolph, A. Stephen K. Hashmi, Synthesis of highly substituted N-(furan-3-ylmethylene)benzenesulfonamides by a gold(I)-catalyzed oxidation/1,2-alkynyl migration/cyclization cascade. Chemistry: A European Journal. ,vol. 20, pp. 14868- 14871 ,(2014) , 10.1002/CHEM.201404229