190370-08-2Relevant academic research and scientific papers
Total synthesis of (-)-epothilone B
May, Scott A.,Grieco, Paul A.
, p. 1597 - 1598 (2007/10/03)
The sixteen-membered ring macrolide (-)-epothilone B 1 has been synthesized by a route which features stereospecific methylation of an (E)-γ,δ-epoxy acrylate, the use of a double asymmetric reaction employing (R,R)-diisopropyltartrate and (E)-crotylboronate, and ring closure by means of an olefin metathesis reaction.
Total syntheses of epothilones A and B via a macrolactonization-based strategy
Nicolaou,Ninkovic,Sarabia,Vourloumis,He,Vallberg,Finlay,Yang
, p. 7974 - 7991 (2007/10/03)
The total syntheses of epothilones A (1) and B (2) and several analogues thereof are described. The reported strategy relies on a macrolactonization approach and features selective epoxidation of the macrocycle double bond in precursors 3 and 4 (Scheme 1), respectively, as well as high convergency and flexibility. Building blocks 9-12 and 15 were constructed by asymmetric processes and coupled via Wittig, aldol, and macrolactonization reactions to afford the basic skeleton of epothilones and that of several of their analogues by a relatively short route. The utilization ofintermediate 14, obtained via a stereoselective Wittig reaction and its Enders coupling to SAMP hydrazone 13 (Scheme 8), in combination with a stereoselective aldol reaction with the modified substrate 69 (Scheme 10) improved the stereoselectivity and efficiency of the total synthesis of these new and highly potent microtubule binding antitumor agents.
