Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin.
| ISSN: |
0040-4020
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|---|---|
| Source: |
Elsevier Journal Backfiles on ScienceDirect 1907 - 2002
|
| Topics: |
Chemistry and Pharmacology
|
| Type of Medium: |
Electronic Resource
|
| URL: |
| _version_ | 1798291338336141313 |
|---|---|
| autor | Cairns, N. Harwood, L.M. Astles, D.P. |
| autorsonst | Cairns, N. Harwood, L.M. Astles, D.P. |
| book_url | http://linkinghub.elsevier.com/retrieve/pii/S0040-4020(01)90370-9 |
| datenlieferant | nat_lic_papers |
| fussnote | Methyl 3-(2-acyloxy-4-methoxyphenyl)propanoates (7), prepared in high yield from 7-methoxycoumarin are key intermediates in general and efficient syntheses of 6-acylcoumarins. Under standard Fries rearrangement conditions (7) undergo highly regioselective para-migration with aluminium chloride in nitromethane. The resulting C-acylated products (8) are converted into 6-acyl-7-methoxycoumarins (4). The scope and limitations of the rearrangement and the application to the total syntheses of the natural linear acylcoumarins, geijerin (4a) and dehydrogeijerin (4b), are described. |
| hauptsatz | hsatz_simple |
| identnr | NLZ175902739 |
| issn | 0040-4020 |
| journal_name | Tetrahedron |
| materialart | 1 |
| package_name | Elsevier |
| publikationsort | Amsterdam |
| publisher | Elsevier |
| reference | 48 (1992), S. 7581-7590 |
| search_space | articles |
| shingle_author_1 | Cairns, N. Harwood, L.M. Astles, D.P. |
| shingle_author_2 | Cairns, N. Harwood, L.M. Astles, D.P. |
| shingle_author_3 | Cairns, N. Harwood, L.M. Astles, D.P. |
| shingle_author_4 | Cairns, N. Harwood, L.M. Astles, D.P. |
| shingle_catch_all_1 | Cairns, N. Harwood, L.M. Astles, D.P. Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin. 0040-4020 00404020 Elsevier |
| shingle_catch_all_2 | Cairns, N. Harwood, L.M. Astles, D.P. Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin. 0040-4020 00404020 Elsevier |
| shingle_catch_all_3 | Cairns, N. Harwood, L.M. Astles, D.P. Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin. 0040-4020 00404020 Elsevier |
| shingle_catch_all_4 | Cairns, N. Harwood, L.M. Astles, D.P. Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin. 0040-4020 00404020 Elsevier |
| shingle_title_1 | Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin. |
| shingle_title_2 | Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin. |
| shingle_title_3 | Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin. |
| shingle_title_4 | Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin. |
| sigel_instance_filter | dkfz geomar wilbert ipn albert fhp |
| source_archive | Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 |
| timestamp | 2024-05-06T08:31:02.398Z |
| titel | Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin. |
| titel_suche | Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin. Methyl 3-(2-acyloxy-4-methoxyphenyl)propanoates (7), prepared in high yield from 7-methoxycoumarin are key intermediates in general and efficient syntheses of 6-acylcoumarins. Under standard Fries rearrangement conditions (7) undergo highly regioselective para-migration with aluminium chloride in nitromethane. The resulting C-acylated products (8) are converted into 6-acyl-7-methoxycoumarins (4). The scope and limitations of the rearrangement and the application to the total syntheses of the natural linear acylcoumarins, geijerin (4a) and dehydrogeijerin (4b), are described. |
| topic | V |
| uid | nat_lic_papers_NLZ175902739 |