187283-46-1Relevant academic research and scientific papers
An efficient total synthesis of (-)-epothilone B
Wang, Jie,Sun, Bing-Feng,Cui, Kai,Lin, Guo-Qiang
, p. 6354 - 6357 (2013/02/23)
An efficient total synthesis of (-)-epothilone B has been achieved in ca. 8% yield over 11 steps from 9 (or 10 steps from 7/8), which features a bissiloxane-tethered ring closing metathesis reaction to approach the trisubstituted (Z) double bond and forms a new basis for further development of an industrial process for epothilone B and ixabepilone.
Towards the synthesis of epothilone A: Enantioselective preparation of the thiazole side-chain and macrocyclic ring closure
Taylor, Richard E.,Haley, Jeffrey D.
, p. 2061 - 2064 (2007/10/03)
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.
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.
Total synthesis of epothilone A: The olefin metathesis approach
Yang,He,Vourloumis,Vallberg,Nicolau
, p. 166 - 168 (2007/10/03)
A flexible alterative route to the total synthesis of the antitumor agent epothilone A has been achieved by a highly convergent strategy involving olefin metathesis as a key step. The strategy may allow the chemical synthesis of a library of designed epothilones for biological screening.
