The Efficient Synthesis of Morphinandienone Alkaloids by Using a Combination of Hypervalent Iodine(III) Reagent and Heteropoly Acid
| Autor: | Hirofumi Tohma, Yasuyuki Kita, Yukiko Shiozaki, Hiromi Hamamoto, Kayoko Hata, Hisanori Nambu |
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| Rok vydání: | 2004 |
| Předmět: |
endocrine system
Molecular Structure Chemistry Silica gel Organic Chemistry Hypervalent molecule General Chemistry Isoquinolines Glaucine Catalysis Coupling reaction Laudanosine chemistry.chemical_compound Alkaloids Morphinans Reagent Yield (chemistry) Oxidizing agent Organic chemistry Acids Oxidation-Reduction Iodine |
| Zdroj: | Chemistry - A European Journal. 10:4977-4982 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.200400358 |
| Popis: | The non-phenolic coupling reaction of benzyltetrahydroisoquinolines (laudanosine derivatives) by using a hypervalent iodine(III) reagent is described. In general, chemical oxidation of laudanosine gives glaucine. In contrast to general chemical oxidizing reagent systems, the novel use of reagent combination of phenyliodine bis(trifluoroacetate) (PIFA), and heteropoly acid (HPA) afforded morphinandienone alkaloids in excellent yields. In order to achieve the coupling reaction with simple reaction procedure, the use of HPA supported on silica gel instead of HPA was demonstrated and sufficient yield was exerted again. The present reagent system, PIFA/HPA, was also applied to the oxidation of other non-phenolic benzyltetrahydroisoquinolines and the high yield conversion to morphinandienones was accomplished. |
| Databáze: | OpenAIRE |
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