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Synthesis and olfactory properties of (−)-(1R,2S)-Georgywood
Tetrahedron: Asymmetry Pub Date : 13 December 2004 , DOI: 10.1016/j.tetasy.2004.11.003
Georg Fráter , Urs Müller , Fridtjof Schröder

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.

中文翻译:

(-)-(1 R,2 S)-乔治木的合成与嗅觉性能

Georgywood的对映体®从(合成ê)-2-甲基-6-亚甲基-壬-2,7-二烯和methacrylaldehyde接着狄尔斯-阿尔德加合物和酸的经典外消旋物分离用旋光活性的氧化Ñ -甲基麻黄碱。转化为最终的酮和嗅觉评估表明,(-)-(1 R,2 S)-对映异构体比其对映体的功效高100倍。绝对构型由构象研究和CD分析确定。
更新日期:2017-01-31
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