185429-83-8Relevant articles and documents
Cyclization of 1,5-dienes: An efficient synthesis of β-Georgywood
Frater, Georg,Schroeder, Fridtjof
, p. 1112 - 1120 (2007)
(Chemical Equation Presented) In the acid-promoted 1,5-diene cyclization of pseudo- to β-Georgywood, the cyclization product is obtained with high selectivity in spite of an unfavorable substituent at the C(2)-position of the diene precursor. Preisomeriza
Synthesis and olfactory properties of (-)-(1R,2S)-Georgywood
Frater, Georg,Mueller, Urs,Schroeder, Fridtjof
, p. 3967 - 3972 (2004)
The enantiomers of Georgywood were synthesized from (E)-2-methyl-6-methylene-nona-2,7-diene and methacrylaldehyde followed by oxidation of the Diels-Alder adduct and classical racemate separation of the acid with optically-active N-methylephedrine. Conversion to the final ketone and olfactory evaluation showed that the (-)-(1R,2S)-enantiomer is more powerful by a factor of >100 than its antipode. The absolute configuration was determined by conformational studies and CD-analysis.
PROCESS FOR THE PREPARATION OF CIS-2-ACETYL-1, 2, 3, 4, 5, 6, 7, 8-OCTAHYDRO-1, 2, 8, 8-TETRAMETHYLNAPHTHALENE
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Page/Page column 5-6, (2008/06/13)
A process of preparation of cis-2-acetyl-1,2,3,4,5,6,7,8-octahydro-1,2,8,8-tetramethylnaphthalene ("?-Georgywood") from cis-1-[1,2-dimethyl-4(4-methyl-pent-3-enyl)-cyclohex-3-enyl]-ethanone (“Ψ -Georgywood"), comprising the reaction of Ψ-Georgywood with more than one molar equivalent of a Lewis acid. The method allows the preparation of isomeric mixtures that contain a much higher proportion of the olfactorily-desirable ?-Georgywood than was previously possible.
