Liebeskind–Srogl cross-coupling on γ-carboxyl-γ-butyrolactone derivatives: application to the side chain of amphidinolides C and F
作者： Johan Fenneteau , Sara Vallerotto , Laurent Ferrié , Bruno Figadère
DOI: 10.1016/J.TETLET.2015.04.035
关键词: Stereochemistry 、 Epoxide 、 Stereoselectivity 、 Amphidinolide F 、 Side chain 、 Chemistry 、 Ketone 、 Reductive elimination 、 Boronic acid 、 Stereocenter
摘要: Abstract The synthetic approach for the C20–C29 and C20–C34 fragments of amphidinolide F C was based on an original Liebeskind–Srogl cross-coupling reaction with a glutamic acid-derived building-block. Further highly diastereoselective reduction ketone achieved by using uncommon Ph 3 SiH/TBAF/HMPA system. side chain built through reductive elimination chiral epoxide to install stereogenic center at C29.
elsevier.com
sci-hub.se 参考文章(58)
Jinkun Huang, Emilio Bunel, Margaret M. Faul, Palladium-Catalyzed α-Vinylation of Carbonyl Compounds Organic Letters. ,vol. 9, pp. 4343- 4346 ,(2007) , 10.1021/OL7019839
Gaël Jalce, Xavier Franck, Blandine Seon-Meniel, Reynald Hocquemiller, Bruno Figadère, Contribution to the total synthesis of caribenolide I Tetrahedron Letters. ,vol. 47, pp. 5905- 5908 ,(2006) , 10.1016/J.TETLET.2006.06.060
Tsutomu Katsuki, K. Barry Sharpless, First practical method for asymmetric epoxidation Journal of the American Chemical Society. ,vol. 102, pp. 5974- 5976 ,(1981) , 10.1021/JA00538A077
Hao Li, Hao Yang, Lanny S. Liebeskind, Synthesis of High Enantiopurity N-Protected α-Amino Ketones by Thiol Ester-Organostannane Cross-Coupling using pH-Neutral Conditions Organic Letters. ,vol. 10, pp. 4375- 4378 ,(2008) , 10.1021/OL8018456
Jared H. Delcamp, Paul E. Gormisky, M. Christina White, Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes Journal of the American Chemical Society. ,vol. 135, pp. 8460- 8463 ,(2013) , 10.1021/JA402891M
Rüdiger Wittenberg, Jiri Srogl, Masahiro Egi, Lanny S. Liebeskind, Ketone synthesis under neutral conditions. Cu(I) diphenylphosphinate-mediated, palladium-catalyzed coupling of thiol esters and organostannanes. Organic Letters. ,vol. 5, pp. 3033- 3035 ,(2003) , 10.1021/OL034962X
Jean Louis Luche, Lanthanides in organic chemistry. 1. Selective 1,2 reductions of conjugated ketones Journal of the American Chemical Society. ,vol. 100, pp. 2226- 2227 ,(1978) , 10.1021/JA00475A040
J. Brad Shotwell, William R. Roush, Synthesis of the C11-C29 fragment of amphidinolide F. Organic Letters. ,vol. 6, pp. 3865- 3868 ,(2004) , 10.1021/OL048381Z
Mahesh P. Paudyal, Nigam P. Rath, Christopher D. Spilling, A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction. Organic Letters. ,vol. 12, pp. 2954- 2957 ,(2010) , 10.1021/OL100959A
Gérard Cahiez, Eric Métais, Enantioselective synthesis of δ-ketobutanolides from (l)-glutamic acid via organomanganese reagents Tetrahedron-asymmetry. ,vol. 8, pp. 1373- 1376 ,(1997) , 10.1016/S0957-4166(97)00099-2