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.
View at publisher
PDF - Registered users only
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.
37 downloads since deposited on 22 May 2012
8 downloads since 12 months
|Item Type:||Journal Article, refereed, original work|
|Communities & Collections:||07 Faculty of Science > Department of Chemistry|
|Dewey Decimal Classification:||540 Chemistry|
|Deposited On:||22 May 2012 07:06|
|Last Modified:||05 Jul 2014 11:16|
|Publisher:||Verlag Helvetica Chimica Acta|
|Funders:||Swiss National Science Foundation , F. Hoffmann-La Roche AG, Basel|
Users (please log in): suggest update or correction for this item
Repository Staff Only: item control page