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Synthese makrocyclischer Ketone durch Ringerweiterung; ein neuer Weg zu$(\pm)$-Muscon


Bienz, Stefan; Hesse, Manfred (2004). Synthese makrocyclischer Ketone durch Ringerweiterung; ein neuer Weg zu$(\pm)$-Muscon. Helvetica Chimica Acta, 70(8):2146-2151.

Abstract

Synthesis of Macrocyclic Ketones by Ring-Enlargement Reactions; a New Path to (+)-Muscone A new synthetic route to macrocyclic ketones is described. Starting from 2-nitrocycloalkanones, the ring-enlarged compounds of the type 4 and 5 were prepared in three steps. Reduction of the NOz group with Bu,SnH and azobisisobutyronitrile led in moderate yields to simple 8-keto-esters which were quantitatively hydrolyzed and decarboxylated to the ketones of the type 8 and 9. The interesting fragrances Exdfone@ @a) and (+)-muscone (9a) were prepared in this way in overall yields of 22 and 18 %, respectively.

Abstract

Synthesis of Macrocyclic Ketones by Ring-Enlargement Reactions; a New Path to (+)-Muscone A new synthetic route to macrocyclic ketones is described. Starting from 2-nitrocycloalkanones, the ring-enlarged compounds of the type 4 and 5 were prepared in three steps. Reduction of the NOz group with Bu,SnH and azobisisobutyronitrile led in moderate yields to simple 8-keto-esters which were quantitatively hydrolyzed and decarboxylated to the ketones of the type 8 and 9. The interesting fragrances Exdfone@ @a) and (+)-muscone (9a) were prepared in this way in overall yields of 22 and 18 %, respectively.

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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:English
Date:2004
Deposited On:25 Aug 2017 13:20
Last Modified:19 Feb 2018 20:47
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/hlca.19870700820

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