- Enantioselective total synthesis of epothilone A using multifunctional asymmetric catalyses
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A catalytic version has now been developed for the enantioselective total synthesis of epothilone A (1). The key is the use of multifunctional asymmetric catalySes for a direct aldol reaction and cyanosilylation. This successful approach demonstrated the usefulness of these reactions for the catalytic asymmetric synthesis of complex molecules.
- Sawada, Daisuke,Shibasaki, Masakatsu
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p. 209 - 213
(2007/10/03)
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- Towards the synthesis of epothilone A: Enantioselective preparation of the thiazole side-chain and macrocyclic ring closure
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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.
- Taylor, Richard E.,Haley, Jeffrey D.
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p. 2061 - 2064
(2007/10/03)
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- Total syntheses of epothilones A and B via a macrolactonization-based strategy
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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.
- Nicolaou,Ninkovic,Sarabia,Vourloumis,He,Vallberg,Finlay,Yang
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p. 7974 - 7991
(2007/10/03)
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- Total synthesis of epothilone A: The olefin metathesis approach
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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.
- Yang,He,Vourloumis,Vallberg,Nicolau
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p. 166 - 168
(2007/10/03)
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