The total synthesis of (+)-tedanolide

被引:50
作者
Ehrlich, Gunnar [1 ]
Hassfeld, Jorma [1 ]
Eggert, Ulrike [1 ]
Kalesse, Markus [1 ]
机构
[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
关键词
D O I
10.1021/ja0659572
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations generate the macrocyclic triketone. In the endgame of the synthesis, four TBS groups are removed in one reaction and a chemo- and stereoselective final step epoxidation generates (+)-tedanolide. Copyright © 2006 American Chemical Society.
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页码:14038 / 14039
页数:2
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