Use of the oxazole-olefin Diels-Alder reaction in the total synthesis of the monoterpene alkaloids (-)-plectrodorine and (+)-oxerine
| Autor: | Masashi Ohba, Emi Shimizu, Rie Izuta |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2006 |
| Předmět: |
Magnetic Resonance Spectroscopy
Spectrophotometry Infrared Stereochemistry Monoterpene Molecular Conformation Alkenes Mass Spectrometry chemistry.chemical_compound Cyclopenta[c]pyridine Plectrodorine Drug Discovery Organic chemistry Dimethyl Sulfoxide Diels-Alder reaction Oxazoles Oxazole Diels–Alder reaction Olefin fiber Chemistry Absolute configuration Total synthesis Monoterpene alkaloid Oxerine General Chemistry General Medicine Intramolecular force Monoterpenes Indicators and Reagents Specific rotation Oxazole-olefin |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 54(1):63-67 |
| ISSN: | 0009-2363 |
| Popis: | A full account of the total synthesis of two monoterpene alkaloids, (-)-plectrodorine [(-)-1] and (+)-oxerine [(+)-3], is presented. The key steps involved are the formation of the oxazole alcohol 10 from the γ-butyrolactone 9 and the intramolecular Diels-Alder reaction of the oxazole-olefins 13a, b. Since the sign of specific rotation for the synthetic (+)-3 was different from that reported for natural oxerine, the absolute configuration of this alkaloid is not yet fully understood. © 2006 Pharmaceutical Society of Japan. |
| Databáze: | OpenAIRE |
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