메뉴 건너뛰기




Volumn 9, Issue 24, 2007, Pages 5083-5086

A general method for the synthesis of nonracemic trans-epoxides: Concise syntheses of trans-epoxide-containing insect sex pheromones

Author keywords

[No Author keywords available]

Indexed keywords

(6Z,9Z,11S,512S) 11,12 EPOXYHENICOSA 6,9 DIENE; (6Z,9Z,11S,512S)-11,12-EPOXYHENICOSA-6,9-DIENE; (6Z,9Z,4S,5S) 4,5 EPOXYNONADECA 6,9 DIENE; (6Z,9Z,4S,5S)-4,5-EPOXYNONADECA-6,9-DIENE; ALDEHYDE; EPOXIDE; SEX PHEROMONE; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

EID: 36849010691     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702273n     Document Type: Article
Times cited : (49)

References (55)
  • 2
    • 0031686721 scopus 로고    scopus 로고
    • (a) Mori, K. Chirality 1998, 10, 578.
    • (1998) Chirality , vol.10 , pp. 578
    • Mori, K.1
  • 25
    • 0001780886 scopus 로고    scopus 로고
    • Paquette, L. A, Ed, John Wiley & Sons, Inc, New York
    • Katsuki, T.; Martin, V. S. Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York, 1996; Vol. 48, pp 1-285.
    • (1996) Organic Reactions , vol.48 , pp. 1-285
    • Katsuki, T.1    Martin, V.S.2
  • 38
    • 0034638388 scopus 로고    scopus 로고
    • 3)).
    • 3)).
  • 39
    • 0028926606 scopus 로고    scopus 로고
    • 3)).
    • 3)).
  • 40
    • 37049057911 scopus 로고    scopus 로고
    • For examples of the diastereoselective addition of organometallic reagents to αl-chloro aldehydes see: (a) Cornforth, J. W, Cornforth, R. H, Mathew, K. K. J. Chem. Soc. 1959, 112
    • For examples of the diastereoselective addition of organometallic reagents to αl-chloro aldehydes see: (a) Cornforth, J. W.; Cornforth, R. H.; Mathew, K. K. J. Chem. Soc. 1959, 112.
  • 46
    • 33644959351 scopus 로고    scopus 로고
    • For a theoretical investigation of nucleophilic addition to an α-chloro aldehyde see:, and references therein
    • For a theoretical investigation of nucleophilic addition to an α-chloro aldehyde see: Cee, V. J.; Cramer, C. J.; Evans, D. A. J. Am. Chem. Soc. 2006, 128, 2920 and references therein.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 2920
    • Cee, V.J.1    Cramer, C.J.2    Evans, D.A.3
  • 47
    • 0034612880 scopus 로고    scopus 로고
    • For the diastereoselective addition of optically pure lithio-vinyl sulfoxides to a racemic α-chloro aldehyde see: Marino, J. P, Anna, L. J, Fernández de la Pradilla, R, Martinez, M. V, Montero, C, Viso, A. J. Org. Chem. 2000, 65, 6462
    • For the diastereoselective addition of optically pure lithio-vinyl sulfoxides to a racemic α-chloro aldehyde see: Marino, J. P.; Anna, L. J.; Fernández de la Pradilla, R.; Martinez, M. V.; Montero, C.; Viso, A. J. Org. Chem. 2000, 65, 6462.
  • 48
    • 36849093293 scopus 로고    scopus 로고
    • 2, EtOH) in excellent yield (94%).
    • 2, EtOH) in excellent yield (94%).
  • 49
    • 36849014680 scopus 로고    scopus 로고
    • D values with those in the literature (see Supporting Information), indicating that there is no erosion of optical purity during the 1,2-addition reactions (10 → 18a-f).
    • D values with those in the literature (see Supporting Information), indicating that there is no erosion of optical purity during the 1,2-addition reactions (10 → 18a-f).
  • 51
    • 0032564684 scopus 로고    scopus 로고
    • 1H NMR spectrum of 19f precluded nOe analysis; however, their chemical shift is consistent with those reported for the H4/H5 resonances in trans-(4S,5S)4,5-epoxynonane (δ 2.61-2.70 ppm) and differ significantly from those reported for cis-(4S,5R)-4,5-epoxynonane δ 2.87-2.96 ppm) in: Besse, P.; Sokoltchik, T.; Veschambre, H. Tetrahedron: Asymmetry 1998, 9, 4441.
    • 1H NMR spectrum of 19f precluded nOe analysis; however, their chemical shift is consistent with those reported for the H4/H5 resonances in trans-(4S,5S)4,5-epoxynonane (δ 2.61-2.70 ppm) and differ significantly from those reported for cis-(4S,5R)-4,5-epoxynonane δ 2.87-2.96 ppm) in: Besse, P.; Sokoltchik, T.; Veschambre, H. Tetrahedron: Asymmetry 1998, 9, 4441.
  • 53
    • 36849079208 scopus 로고    scopus 로고
    • 6.7 alkene function in 26. Lindlar reduction of 25 or 26 at room temperature led to the production of unidentified byproducts.
    • 6.7 alkene function in 26. Lindlar reduction of 25 or 26 at room temperature led to the production of unidentified byproducts.
  • 54
    • 36849027071 scopus 로고    scopus 로고
    • We thank Professor Gerhard Gries for kindly providing an authentic sample of, -1 and Regine Gries for carrying out the comparative GC analysis with our synthetic material
    • We thank Professor Gerhard Gries for kindly providing an authentic sample of ( - )-1 and Regine Gries for carrying out the comparative GC analysis with our synthetic material.
  • 55
    • 36849066838 scopus 로고    scopus 로고
    • Field-studies will be carried out by the Forest Research Institute in Eberswalde, Germany. The results of these studies will be published in due course
    • Field-studies will be carried out by the Forest Research Institute in Eberswalde, Germany. The results of these studies will be published in due course.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.