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Cover Picture: Conception, Characterization and Correlation of New Marine Odorants (Eur. J. Org. Chem. 19/2003)
Author(s) -
Kraft Philip,
Eichenberger Walter
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390241
Subject(s) - chemistry , odor , aromatization , demethylation , stereochemistry , organic chemistry , biochemistry , gene expression , dna methylation , gene , catalysis
The cover picture shows , in front of a water surface and with an electon‐density cloud in the form of a water droplet, the best marine odorant of a series of substituted benzo[ b ][1,4]dioxepinones and 2,3‐dihydro‐1 H ‐5,9‐dioxacyclohepta[ f ]indenones. It posseses a very intense and diffusive, marine odor with floral‐aldehydic nuances and an exceptionally low odor threshold of 0.014 ng/L air! A beam highlights the hydrophobic binding centre 6.3 Å apart from the aromatic ring binding site. This feature accounts for its exceptional odor characteristics as was rationalized by an olfactophore model constructed on the basis of 20 measured odor thresholds. A synthetic sequence consisting of PPA‐mediated Friedel−Crafts acylation, Clemmensen reduction, demethylation, Williamson ether synthesis employing 1‐chloro‐2‐(chloromethyl)prop‐1‐ene and subsequent ruthenium tetroxide oxidation opens up a simple, straightforward access to these marine odorants and related structures. Details are discussed in the article by P. Kraft and W. Eichenberger on p. 3735 ff.