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Titolo:
Asymmetric synthesis of both enantiomers of point-difluorinated-eldanolide, analogues of insect sex pheromone
Autore:
Itoh, T; Kudo, K; Tanaka, N; Zagatti, P; Renou, M;
Indirizzi:
Okayama Univ, Fac Educ, Dept Chem, Okayama 7008530, Japan Okayama Univ Okayama Japan 7008530 uc, Dept Chem, Okayama 7008530, Japan INRA, Unite Phytopharm & Mediateurs Chim, F-78026 Versailles, France INRAVersailles France F-78026 diateurs Chim, F-78026 Versailles, France
Titolo Testata:
ENANTIOMER
fascicolo: 1, volume: 6, anno: 2001,
pagine: 43 -
SICI:
1024-2430(2001)6:1<43:ASOBEO>2.0.ZU;2-8
Fonte:
ISI
Lingua:
ENG
Soggetto:
ELDANA-SACCHARINA WLK; SUGAR-CANE BORER; HALOACETATE ANALOGS; ORGANOFLUORINE COMPOUNDS; RADICAL CYCLIZATION; INHIBITION;
Keywords:
partly fluorinated pheromone analogue; aymmetric synthesis; radical cyclization; lipase-catalyzed reaction;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
18
Recensione:
Indirizzi per estratti:
Indirizzo: Itoh, T Okayama Univ, Fac Educ, Dept Chem, 2-5-1 Shikata Cho, Okayama 7008530, Japan Okayama Univ 2-5-1 Shikata Cho Okayama Japan 7008530 08530, Japan
Citazione:
T. Itoh et al., "Asymmetric synthesis of both enantiomers of point-difluorinated-eldanolide, analogues of insect sex pheromone", ENANTIOMER, 6(1), 2001, pp. 43

Abstract

Substitution of two fluorine atoms on organic molecules is expected to alter both chemical reactivity and biological activity due to the strong electron-with drawing 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 ethergave 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.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/11/20 alle ore 12:43:16