Asymmetric Synthesis and Absolute Configuration of Streptophenazine G

被引:27
作者
Yang, Zhicai [1 ]
Jin, Xiaomin [1 ]
Guaciaro, Michael [1 ]
Molino, Bruce F. [1 ]
机构
[1] AMRI, Dept Med Chem, Albany, NY 12212 USA
关键词
STREPTOMYCES-ANTIBIOTICUS; AGGREGATION PHEROMONE; N-ACYLOXAZOLIDINONES; TRIBOLIUM-CASTANEUM; STRAIN; ALPHA;
D O I
10.1021/jo202642a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric synthesis of the antibacterial natural product, streptophenazine G, has been achieved by employing asymmetric alkylation and asymmetric aldol reactions using chiral oxazolidinones as the key steps. The originally proposed structure for streptophenazine G has been revised, and its absolute configuration has been determined to be 1'S,2'R,6'S. The asymmetric total synthesis of 6'-epi-streptophenazine G is also described.
引用
收藏
页码:3191 / 3196
页数:6
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