Concise Synthesis of Anti-HIV-1 Active (+)-Inophyllum B and (+)-Calanolide A by Application of (−)-Quinine-Catalyzed Intramolecular Oxo-Michael Addition
| Autor: | Takuya Kumamoto, Etsuko Sekino, Tomoko Ikeda, Tomohiro Tanaka, Tsutomu Ishikawa |
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| Rok vydání: | 2004 |
| Předmět: |
Molecular Structure
Quinine biology Intramolecular reaction Anti-HIV Agents Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Cinchona Stereoisomerism Context (language use) Calanolide A biology.organism_classification Pyranocoumarins Chemical synthesis Catalysis Coumarins Michael reaction Stereoselectivity |
| Zdroj: | The Journal of Organic Chemistry. 69:2760-2767 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo035753t |
| Popis: | (-)-Quinine-catalyzed intramolecular oxo-Michael addition (IMA) of 7-hydroxy-5-methoxy-8-tigloylcoumarins was developed for the enantioselective construction of 2,3-dimethyl-4-chromanone systems in the context of the asymmetric synthesis of anti-HIV-1 active Calophyllum coumarins. Combination of the IMA and MgI(2)-assisted demethylation of the 5-methoxy group along with isomerization of the formed chromanone systems as key steps successfully led to the concise synthesis of (+)-inophyllum B and (+)-calanolide A, possible candidates for AIDS drugs. Further examination of the asymmetric IMA with cinchona alkaloids lacking a methoxy group on the quinoline skeleton suggested the influence of the methoxy substituent on stereoselectivity at the stereogenic centers of the chromanone systems. |
| Databáze: | OpenAIRE |
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