UZH-Logo

Maintenance Infos

Synthese eines cyclischen Depsipeptides mittels Amidcyclisierung


Obrecht, Daniel; Heimgartner, Heinz (1984). Synthese eines cyclischen Depsipeptides mittels Amidcyclisierung. Helvetica Chimica Acta, 67:526-533.

Abstract

Synthesis of a Cyclic Depsipeptide via an Amide Cyclization
The synthesis of (S)-Pms-(R)-Pro-(S)-Ala-Aib-N(CH3)2 (12) has been achieved according to Scheme 3. For the formation of fragment 11, the reaction of Z-alanine (Z = benzyloxycarbonyl) and 3-dimethylamino-2,2-dimethyl-2H-azirine (1) has been used, whereby 1 serves as an aminoisobutyric-acid dimethylamide (Aib-N(CH3)2) equivalent. Treatment of a suspension of 12 in toluene with HC1 gas at 100° led to the cyclic depsipeptide 13 in 72% yield (Scheme 4). In presence of water, the acid 14 was isolated as the sole product. A mechanism for the formation of 13 and 14 via an oxazolinone intermediate, is postulated in Scheme 4.

Synthesis of a Cyclic Depsipeptide via an Amide Cyclization
The synthesis of (S)-Pms-(R)-Pro-(S)-Ala-Aib-N(CH3)2 (12) has been achieved according to Scheme 3. For the formation of fragment 11, the reaction of Z-alanine (Z = benzyloxycarbonyl) and 3-dimethylamino-2,2-dimethyl-2H-azirine (1) has been used, whereby 1 serves as an aminoisobutyric-acid dimethylamide (Aib-N(CH3)2) equivalent. Treatment of a suspension of 12 in toluene with HC1 gas at 100° led to the cyclic depsipeptide 13 in 72% yield (Scheme 4). In presence of water, the acid 14 was isolated as the sole product. A mechanism for the formation of 13 and 14 via an oxazolinone intermediate, is postulated in Scheme 4.

Citations

Downloads

0 downloads since deposited on 02 Jul 2014
0 downloads since 12 months

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1984
Deposited On:02 Jul 2014 14:36
Last Modified:05 Apr 2016 17:56
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel
Permanent URL: https://doi.org/10.5167/uzh-96882

Download

[img]
Content: Published Version
Language: German
Filetype: PDF - Registered users only
Size: 512kB

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations