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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.

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.

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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:21 Nov 2017 17:23
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel

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