Total synthesis of epothilone A |
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Authors: | Zhu B Panek J S |
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Affiliation: | Department of Chemistry and the Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, Boston University, Massachusetts 02215, USA. |
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Abstract: | [reaction: see text]Epothilones A (1) and B (2) are potent antitumor natural products with a Taxol-like mechanism of action. A total synthesis of epothilone A (1) is reported, which utilized chiral silane-based bond construction methodology to introduce the key C-6 and C-7 stereocenters of fragment 4. The C-15 stereocenter of fragment 5 was established by a lipase-mediated kinetic resolution. The fragments were assembled with a Suzuki coupling reaction and an aldol condensation and cyclized with a Yamaguchi-type macrolactonization reaction. |
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