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Synthese makrocyclischer, $\alpha, \beta$-ungesättigter y-Oxolactone durch Ringerweiterungsreaktionen; ein neuer Weg zum makrocyclischen Lacton-Antibiotikum A 26771 B


Bienz, Stefan; Hesse, Mauhad (1987). Synthese makrocyclischer, $\alpha, \beta$-ungesättigter y-Oxolactone durch Ringerweiterungsreaktionen; ein neuer Weg zum makrocyclischen Lacton-Antibiotikum A 26771 B. Helvetica Chimica Acta, 70(5):1333-1340.

Abstract

A new synthetic route to the a$- unsaturated y-oxolactones 2a and 2b, involving two ring-enlargement reactions, is described. Ring opening of bicyclic a- nitroketones of the type 3 gave ring-enlarged compounds of the type 4 which were converted to monoprotected diketones of the type 10 by using a variation of the Nefreaction as a key step. Macrocyclic lactones of the type I1 were obtained by Baeyer-Viffiger oxidation and converted into compounds of the type 2. The conversion of 2b to the macrocyclic lactone antibiotic A 26 771 B (1) is already described in the literature.

Abstract

A new synthetic route to the a$- unsaturated y-oxolactones 2a and 2b, involving two ring-enlargement reactions, is described. Ring opening of bicyclic a- nitroketones of the type 3 gave ring-enlarged compounds of the type 4 which were converted to monoprotected diketones of the type 10 by using a variation of the Nefreaction as a key step. Macrocyclic lactones of the type I1 were obtained by Baeyer-Viffiger oxidation and converted into compounds of the type 2. The conversion of 2b to the macrocyclic lactone antibiotic A 26 771 B (1) is already described in the literature.

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Additional indexing

Other titles:Synthesis of macrocyclic $\alpha,\beta$-unsaturated y-oxolactones by ring-enlargement reactions; a new path to the macrocyclic lactone antibiotic A 26771 B
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1987
Deposited On:25 Aug 2017 13:41
Last Modified:25 Aug 2017 13:41
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.19870700515

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