Organocatalytic asymmetric syntheses of inthomycins A, B and C

Organocatalytic asymmetric syntheses of inthomycins A, B and C

The total syntheses of (+)-inthomycin A, (+)-inthomycin B and (-)-inthomycin C, the oxazole-triene antibiotics isolated from Streptomyces sp., have been accomplished via the highly enantio- and stereoselective construction of the C1-C7 (iododienyl)aldol units by taking advantage of a Cinchona alkalo...

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Veröffentlicht in:Organic & biomolecular chemistry 2012-10, Vol.10 (40), p.8164-8174
Hauptverfasser: Yoshino, Madoka, Eto, Kohei, Takahashi, Keisuke, Ishihara, Jun, Hatakeyama, Susumi
Format: Artikel
Sprache:eng
Schlagworte:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Catalysis
Cinchona Alkaloids - chemistry
Fatty Acids, Unsaturated - chemical synthesis
Fatty Acids, Unsaturated - chemistry
Molecular Structure
Oxazoles - chemical synthesis
Oxazoles - chemistry
Stereoisomerism
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Zusammenfassung:The total syntheses of (+)-inthomycin A, (+)-inthomycin B and (-)-inthomycin C, the oxazole-triene antibiotics isolated from Streptomyces sp., have been accomplished via the highly enantio- and stereoselective construction of the C1-C7 (iododienyl)aldol units by taking advantage of a Cinchona alkaloid-catalyzed asymmetric β-lactone synthesis and their isomerisation-free Stille coupling with (E)-5-(3-(tributylstannyl)allyl)oxazole.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob26084k