Asymmetric synthesis of the fully functional macrolide core of salicylihalamide:: Remote control of olefin geometry during RCM

被引:122
作者
Fürstner, A [1 ]
Thiel, OR [1 ]
Blanda, G [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
D O I
10.1021/ol006646d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A catalysis-based approach to the core region 24 of the antitumor agents salicylihalamides A and B is reported. Key steps are two asymmetric hydrogenations of beta -keto esters 13 and 16 catalyzed by [(R)-BINAP-RuCl2](2). NEt3 and an RCM-based macrocyclization effected by the NHC-containing ruthenium carbene 21. The stereochemical outcome of the tatter reaction is controlled by remote substituents on the phenolic OH group of the cyclization precursor 23.
引用
收藏
页码:3731 / 3734
页数:4
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