Application of Pd(0)-Catalyzed Intramolecular Oxazine Formation to the Efficient Total Synthesis of (−)-Anisomycin

Application of Pd(0)-Catalyzed Intramolecular Oxazine Formation to the Efficient Total Synthesis of (−)-Anisomycin

The enantioselective total synthesis of (−)-anisomycin, a potent antibiotic agent, has been achieved. The key steps are a Pd(0)-catalyzed stereoselective intramolecular oxazine formation from d-tyrosine and pyrrolidine formation by catalytic hydrogenation of the oxazine.

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Veröffentlicht in:Organic letters 2007-08, Vol.9 (18), p.3627-3630
Hauptverfasser: Joo, Jae-Eun, Lee, Kee-Young, Pham, Van-Thoai, Tian, Yong-Shou, Ham, Won-Hun
Format: Artikel
Sprache:eng
Schlagworte:
Anisomycin - chemical synthesis
Anisomycin - chemistry
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Catalysis
Molecular Structure
Oxazines - chemical synthesis
Oxazines - chemistry
Palladium - chemistry
Pyrrolidines - chemistry
Tyrosine - chemistry
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Zusammenfassung:The enantioselective total synthesis of (−)-anisomycin, a potent antibiotic agent, has been achieved. The key steps are a Pd(0)-catalyzed stereoselective intramolecular oxazine formation from d-tyrosine and pyrrolidine formation by catalytic hydrogenation of the oxazine.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol701519b