Synthesis and Antifungal Activity of Novel 14-Membered Benzomacrolides as Galbonolide Analogues
| Autor: | Koji Yamada, Yuichi Sugimoto, Hideki Jona, Rie Bamba-Nagano, Hajime Morishima, Shunji Sakuraba, Terutaka Hashizume, Hiroki Sakoh, Hideaki Imamura |
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| Rok vydání: | 2004 |
| Předmět: |
Antifungal
Galbonolide Antifungal Agents medicine.drug_class Chemistry Stereochemistry Fungi Total synthesis Stereoisomerism Microbial Sensitivity Tests General Chemistry General Medicine Ring (chemistry) Chloride Catalysis Kinetic resolution Lactones chemistry.chemical_compound Drug Discovery medicine Conjugated diene Macrolides Benzene Oxidation-Reduction medicine.drug |
| Zdroj: | ChemInform. 35 |
| ISSN: | 1522-2667 0931-7597 |
| DOI: | 10.1002/chin.200430207 |
| Popis: | Asymmetric total synthesis of benzene analogues of galbonolide, a 14-membered antifungal macrolide, possessing a benzene ring instead of a conjugated diene structure, was achieved starting from chiral 1-aryl-1-propanol obtained by enzyme-catalyzed kinetic resolution with high enantioselectivity. Representatively, a method for the introduction of a methylthio and chloride function at the vinyl position was also established. The resulting analogues unfortunately exhibited very little antifungal potency in comparison with galbonolide A. |
| Databáze: | OpenAIRE |
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