A novel oxy-oxonia(azonia)-cope reaction: serendipitous discovery and its application to the synthesis of macrocyclic musks.
Chem Biodivers
; 11(10): 1608-28, 2014 Oct.
Article
em En
| MEDLINE
| ID: mdl-25329787
ABSTRACT
This brief review, including new experimental results, is the summary of a talk at the GDCh conference 'flavors & fragrances 2013' in Leipzig, Germany, 11th-13th September, 2013. Musk odorants are indispensable in perfumery to lend sensuality to fine fragrances, a nourishing effect to cosmetics, and a comforting feeling to laundry. We have recently found serendipitously a new oxy-oxonia-Cope rearrangement. In this account, we review the background of oxonia-sigmatropic rearrangements and the discovery of this novel reaction. Special attention is focused on the versatile lactone and lactam formation reactions via [n+4] ring enlargement and the macrocyclization in the synthesis of new macrocyclic musks. The synthesized structures provide new insights into the structure-odor relationships of musks.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Perfumes
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Ácidos Graxos Monoinsaturados
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Compostos Macrocíclicos
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Difosfonatos
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Peróxido de Hidrogênio
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Acetatos
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article