Asymmetric Total Synthesis of Botcinins C, D, and F

Asymmetric Total Synthesis of Botcinins C, D, and F

Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and SmI2-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral...

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Veröffentlicht in:Organic letters 2008-07, Vol.10 (14), p.3153-3156
Hauptverfasser: Fukui, Hiroki, Shiina, Isamu
Format: Artikel
Sprache:eng
Schlagworte:
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Botrytis - chemistry
Magnaporthe - drug effects
Molecular Structure
Plant Diseases - microbiology
Pyrones - chemical synthesis
Pyrones - chemistry
Pyrones - pharmacology
Stereoisomerism
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Zusammenfassung:Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and SmI2-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801066y