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.
Enantioselective syntheses of georgyone, arborone, and structural relatives. Relevance to the molecular-level understanding of olfaction
Hong, Sungwoo,Corey
, p. 1346 - 1352 (2007/10/03)
Georgyone (1) and arborone (2), powerful woody odorants, have been synthesized enantioselectively along with their enantiomers. Several structural relatives of 1 and 2 have also been made enantioselectivity in order to probe the molecular details of the b