Stereoselective total synthesis of (-)-borrelidin

被引:85
|
作者
Vong, BG [1 ]
Kim, SH [1 ]
Abraham, S [1 ]
Theodorakis, EA [1 ]
机构
[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
关键词
hydrostannation; macrolactonization; natural products; synthetic methods; total synthesis;
D O I
10.1002/anie.200460203
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A convergent synthesis of (-)-borrelidin (1) is reported based on the retrosynthetic disconnections indicated in the picture. Highlights of the strategy include the construction of a strained enynone-containing macrolide and the installation of a cyano group in a regioselective manner by a novel molybdenum-catalyzed hydrostannation of the alkyne.
引用
收藏
页码:3947 / 3951
页数:5
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