Synthesis of the four stereoisomers of 6-acetoxy-19-methylnonacosane, the most potent component of the female sex pheromone of the new world screwworm fly, with special emphasis on partial racemization in the course of catalytic hydrogenation

European Journal of Organic Chemistry

Volumn , Issue 5, 2004, Pages 1089-1096

  Mori, Kenji ^a   Ohtaki, Takashi ^b   Ohrui, Hiroshi ^b   Berkebile, Dennis R ^c   Carlson, David A ^d  

^a Fuji Flavor Co Ltd   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c AGRICULTURAL RESEARCH SERVICE   (United States)

^d CENTER FOR MEDICAL   (United States)

Author keywords

Hydrogenation; Liquid chromatography; Natural products; Pheromones

Indexed keywords

6 ACETOXY 19 METHYLNONACOSANE; ALCOHOL DERIVATIVE; ALKANE DERIVATIVE; CITRONELLAL; OXIDE; PLATINUM DERIVATIVE; SEX PHEROMONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENANTIOMER; FLY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; ISOMER; RACEMIZATION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 4544249267     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300669     Document Type: Article

References (12)

1. J. G. Pomonis, L. Hammack, H. Hakk, J. Chem. Ecol. 1993, 19, 985-1007.
2. A. Furukawa, C. Shibata, K. Mori, Biosci. Biotechnol. Biochem. 2002, 66, 1164-1169.
3. K. Mori, Biosci. Biotechnol. Biochem. 2003, 67, 2224-2231.
4. D. A. Carlson, D. R. Berkebile, S. R. Skoda, K. Mori, Naturwissenschaften, in press.
5. H. Ohrui, H. Terashima, K. Imaizumi, K. Akasaka, Proc. Japan Acad. Ser. B 2002, 78, 69-72.
6. Y. Shirai, M. Seki, K. Mori, Eur. J. Org. Chem. 1999, 3139-3145.
7. C. Fouquet, M. Schlosser, Angew. Chem. Int. Ed. Engl. 1974, 13, 82-83.
8. T. Tashiro, K. Akasaka, H. Ohrui, E. Fattorusso, K. Mori, Eur. J. Org. Chem. 2002, 3659-3665.
9. A. P. C. Kieboom, E. van Rantwijk, Hydrogenation and Hydrogenolysis in Synthetic Organic Chemistry, Delft University Press, 1977, p. 41.
10. K. Mori, Eur. J. Org. Chem. 1998, 1479-1489.
11. R. Nishida, H. Fukami, Mem. Coll. Agric., Kyoto Univ. 1983, 122, 1-24.
12. K. Imaizumi, H. Terasima, K. Akasaka, H. Ohrui, Anal. Sci. 2003, 19, 1243-1249.