Total synthesis of epothilone A

被引:70
作者
Zhu, B
Panek, JS
机构
[1] Boston Univ, Metcalf Ctr Sci & Engn, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Metcalf Ctr Sci & Engn, Ctr Streamlined Synth, Boston, MA 02215 USA
关键词
D O I
10.1021/ol006104w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] 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 end cyclized with a Yamaguchi type macrolactonization reaction.
引用
收藏
页码:2575 / 2578
页数:4
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