Asymmetric Synthesis and Absolute Configuration of Streptophenazine G

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 abso...

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Veröffentlicht in:Journal of organic chemistry 2012-04, Vol.77 (7), p.3191-3196
Hauptverfasser: Yang, Zhicai, Jin, Xiaomin, Guaciaro, Michael, Molino, Bruce F
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo202642a