214892-55-4Relevant academic research and scientific papers
The formal total synthesis of epothilone A
Kalesse, Markus,Quitschalle, Monika,Claus, Eckhard,Gerlach, Kai,Pahl, Axel,Meyer, Hartmut H.
, p. 2817 - 2823 (2007/10/03)
The formal total synthesis of epothilone A is described. The key steps in the synthesis of the northern hemisphere are a Z-selective ten-membered ring-closing metathesis reaction (RCM) and the diastereoselective alkylation at C8. Aldehyde 3 is formed by introduction of the thiazole moiety by a Wittig reaction and subsequent functional group transformation. An efficient route to keto acid 5 is described.
Synthesis of the northern hemisphere of epothilone A by a ten-membered ring closing metathesis reaction
Gerlach, Kai,Quitschalle, Monika,Kalesse, Markus
, p. 3553 - 3556 (2007/10/03)
The synthesis of the strained epothilone analog containing a ten- membered ring as well as the northern hemisphere of epothilone A is described. This approach, using the ring closing metathesis reaction, is a solution to the lack of stereocontrol observed
Synthesis of the C7-C17 segment of epothilones by a 10-membered ring closing metathesis reaction
Gerlach, Kai,Quitschalle, Monika,Kalesse, Markus
, p. 1108 - 1110 (2007/10/03)
The synthesis of the C7-C17 segment of epothilones employing a ring closing metathesis is described. Our approach utilizes the stereoselective methylation of the 10-membered lactone, generated by ring closing metathesis, for introducing the methyl group at C8 and provides an efficient access to strained epothilone derivatives, as well as to the C7-C17 segment of epothilones.
