Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-62022
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.
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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 > Institute of Organic Chemistry|
|Deposited On:||22 May 2012 09:06|
|Last Modified:||28 Feb 2014 21:10|
|Publisher:||Verlag Helvetica Chimica Acta|
|Funders:||Swiss National Science Foundation , F. Hoffmann-La Roche AG, Basel|
|Citations:||Web of Science®. Times Cited: 1|
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