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Enantiomer

Title:		"Asymmetric synthesis of both enantiomers of point-difluorinated-eldanolide, analogues of insect sex pheromone"
Author(s):		Itoh T; Kudo K; Tanaka N; Zagatti P; Renou M;
Address:		"Department of Chemistry, Faculty of Education, Okayama University, Japan. titoh@cc.okayama-u.ac.jp"
Journal Title:		Enantiomer
Year:		2001
Volume:		6
Issue:		1
Page Number:		43 - 49
DOI:
ISSN/ISBN:		1024-2430 (Print) 1024-2430 (Linking)
Abstract:		"Substitution of two fluorine atoms on organic molecules is expected to alter both chemical reactivity and biological activity due to the strong electron-withdrawing nature of fluorine. The synthesis of partly gem-difluorinated compounds remains a significant challenge to synthetic organic chemists. We report that [2,3]-Wittig rearrangement of 1,1,2-trifluoroallylic ether gave a new type of partly gem-difluorinated allylic alcohol: 6-methyl-4,4,5-trifluorohept-1,5-dien-3-ol, 3, in a highly stereoselective fashion, and optical resolution of alcohol 3 was accomplished via lipase PS(PCL)-catalyzed reaction. Using this alcohol as the starting material, the first asymmetric synthesis of both enantiomers of point-fluorinated-eldanolides, 2,2,5,5,6-pentafluoroeldanolide 1 and 5,5,6-trifluoroeldanolide 2, analogues of the sex pheromone of the male African sugarcane borer, has been demonstrated"
Keywords:		Alkadienes/*chemical synthesis/chemistry Animals Fluorine/*chemistry Insecta Sex Attractants/*chemical synthesis/chemistry;
Notes:		"MedlineItoh, T Kudo, K Tanaka, N Zagatti, P Renou, M eng 2001/07/04 Enantiomer. 2001; 6(1):43-9"