Header

UZH-Logo

Maintenance Infos

Transformation of 5-Hydroxy- to (5-Chloropentanoyl)amino Derivatives under ‘Direct Amide Cyclization’ Conditions


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.

Abstract

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.

Abstract

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.

Statistics

Citations

Dimensions.ai Metrics
1 citation in Web of Science®
1 citation in Scopus®
1 citation in Microsoft Academic
Google Scholar™

Altmetrics

Downloads

83 downloads since deposited on 22 May 2012
17 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 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:18 Aug 2018 04:54
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:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSwiss National Science Foundation
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche AG, Basel

Download