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Iliev, Boyan; Verma, Sanjiv; Linden, Anthony; Heimgartner, Heinz (2006). Transformation of 5-Hydroxy- to (5-Chloropentanoyl)amino Derivatives under ‘Direct Amide Cyclization’ Conditions. Helvetica Chimica Acta, 89(2):352-359.
The application of the ‘direct amide cyclization’ conditions to the linear delta-hydroxy diamide 11 is described (Scheme 3). Instead of the cyclization to the expected nine-membered cyclodepsipeptide, only the chloro acid 12 was obtained. Its formation could be explained by consecutive formation of the 1,3-oxazol-5(4H)-one 16 and the six-membered imino lactone 17 as intermediates (Scheme 4). The spontaneous isomerization of the latter gave 12 in a good yield.
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry Life Sciences > Drug Discovery Physical Sciences > Physical and Theoretical Chemistry Physical Sciences > Organic Chemistry Physical Sciences > Inorganic Chemistry |
| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
| Language: | English |
| Date: | 2006 |
| Deposited On: | 22 May 2012 07:06 |
| Last Modified: | 07 Mar 2025 02:40 |
| Publisher: | Verlag Helvetica Chimica Acta |
| ISSN: | 0018-019X |
| Funders: | Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel |
| OA Status: | Green |
| Publisher DOI: | https://doi.org/10.1002/hlca.200690038 |
| Project Information: |
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Iliev, Boyan