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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Bibliographic Details
Published inOrganic letters Vol. 9; no. 18; pp. 3627 - 3630
Main Authors Joo, Jae-Eun, Lee, Kee-Young, Pham, Van-Thoai, Tian, Yong-Shou, Ham, Won-Hun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 30.08.2007
Amer Chemical Soc
Subjects
Anisomycin - chemical synthesis
Anisomycin - chemistry
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Catalysis
Chemistry
Chemistry, Organic
Molecular Structure
Oxazines - chemical synthesis
Oxazines - chemistry
Palladium - chemistry
Physical Sciences
Pyrrolidines - chemistry
Science & Technology
Tyrosine - chemistry
ANISOMYCIN
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/ol701519b