Synthesis of Cyclic ?-Diones, a Class of Natural Flavor Compounds
A practical and generally applicable synthesis of the important flavor ingredients corylone (5) and its alkyl homologues 11, 13, 15, and 16 is described, based on alkylation of methyl 4-methoxyacetoacetate (6) with an ?-chloro-ketone and subsequent cyclization, hydrolysis, and decarboxylat...
| Main Authors: | , , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1992-10-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/2168 |
| _version_ | 1818282022655754240 |
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| author | Hannes Wild Ulrich Huber Georg Fráter |
| author_facet | Hannes Wild Ulrich Huber Georg Fráter |
| author_sort | Hannes Wild |
| collection | DOAJ |
| description |
A practical and generally applicable synthesis of the important flavor ingredients corylone (5) and its alkyl homologues 11, 13, 15, and 16 is described, based on alkylation of methyl 4-methoxyacetoacetate (6) with an ?-chloro-ketone and subsequent
cyclization, hydrolysis, and decarboxylation. The one-pot transformation of methyl 4-chloroacetoacetate to 17 through four consecutive steps is demonstrated. The principle has also been used to prepare the six-membered ring analogues 23 and 24.
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| first_indexed | 2024-12-13T00:14:24Z |
| format | Article |
| id | doaj.art-163ccb7c52f0492699ddbd0afc94bf31 |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-12-13T00:14:24Z |
| publishDate | 1992-10-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-163ccb7c52f0492699ddbd0afc94bf312022-12-22T00:05:50ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241992-10-014610Synthesis of Cyclic ?-Diones, a Class of Natural Flavor CompoundsHannes WildUlrich HuberGeorg Fráter A practical and generally applicable synthesis of the important flavor ingredients corylone (5) and its alkyl homologues 11, 13, 15, and 16 is described, based on alkylation of methyl 4-methoxyacetoacetate (6) with an ?-chloro-ketone and subsequent cyclization, hydrolysis, and decarboxylation. The one-pot transformation of methyl 4-chloroacetoacetate to 17 through four consecutive steps is demonstrated. The principle has also been used to prepare the six-membered ring analogues 23 and 24. https://www.chimia.ch/chimia/article/view/2168 |
| spellingShingle | Hannes Wild Ulrich Huber Georg Fráter Synthesis of Cyclic ?-Diones, a Class of Natural Flavor Compounds CHIMIA |
| title | Synthesis of Cyclic ?-Diones, a Class of Natural Flavor Compounds |
| title_full | Synthesis of Cyclic ?-Diones, a Class of Natural Flavor Compounds |
| title_fullStr | Synthesis of Cyclic ?-Diones, a Class of Natural Flavor Compounds |
| title_full_unstemmed | Synthesis of Cyclic ?-Diones, a Class of Natural Flavor Compounds |
| title_short | Synthesis of Cyclic ?-Diones, a Class of Natural Flavor Compounds |
| title_sort | synthesis of cyclic diones a class of natural flavor compounds |
| url | https://www.chimia.ch/chimia/article/view/2168 |
| work_keys_str_mv | AT hanneswild synthesisofcyclicdionesaclassofnaturalflavorcompounds AT ulrichhuber synthesisofcyclicdionesaclassofnaturalflavorcompounds AT georgfrater synthesisofcyclicdionesaclassofnaturalflavorcompounds |