Towards the synthesis of epothilone A: Enantioselective preparation of the thiazole sidechain and macrocyclic ring closure
RE Taylor, JD Haley
Index: Taylor, Richard E.; Haley, Jeffrey D. Tetrahedron Letters, 1997 , vol. 38, # 12 p. 2061 - 2064
Full Text: HTML
Citation Number: 91
Abstract
A synthetic approach to a new class of microtubule-stabilizing natural products is described which employs a macrocyclic olefination strategy to cyclize the 16-membered lactone ring. The C13 C19 thiazole subunit of epothilone A and B is prepared in high enantioselectivity using a catalytic asymmetric allylation reaction.
Related Articles:
An Efficient Total Synthesis of (−)-Epothilone B
[Wang, Jie; Sun, Bing-Feng; Cui, Kai; Lin, Guo-Qiang Organic Letters, 2012 , vol. 14, # 24 p. 6354 - 6357]
Total synthesis of epothilones B and D: Stannane equivalents for β-keto ester dianions
[Keck, Gary E.; Giles, Robert L.; Cee, Victor J.; Wager, Carrie A.; Yu, Tao; Kraft, Matthew B. Journal of Organic Chemistry, 2008 , vol. 73, # 24 p. 9675 - 9691]
Total Synthesis of (−)??Epothilone A
[Schinzer, Dieter; Bauer, Armin; Boehm, Oliver M.; Limberg, Anja; Cordes, Martin Chemistry - A European Journal, 1999 , vol. 5, # 9 p. 2483 - 2491]
Total synthesis of 12, 13-desoxyepothilone B (Epothilone D)
[Broadrup, Robert L.; Sundar, Hema M.; Swindell, Charles S. Bioorganic Chemistry, 2005 , vol. 33, # 2 p. 116 - 133]
Total syntheses of epothilones A and B via a macrolactonization-based strategy
[Nicolaou; Ninkovic; Sarabia; Vourloumis; He; Vallberg; Finlay; Yang Journal of the American Chemical Society, 1997 , vol. 119, # 34 p. 7974 - 7991]