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Volumn , Issue 20, 2003, Pages 3958-3968

Electrophilic Cyclization of 1,6-Dienes Containing an Allylsilane Moiety - Enantioselective Synthesis of cis- and trans-γ-Irone

Author keywords

Cyclization; Fragrances; Synthetic methods; Terpenoids; Total synthesis

Indexed keywords

CYCLOHEXANE DERIVATIVE; GAMMA IRONE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; MERCURY DERIVATIVE; METHYLENECYCLOHEXANE DERIVATIVE; SILANE DERIVATIVE; TRIFLUOROACETATE MERCURY; UNCLASSIFIED DRUG;

EID: 0242291960     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300276     Document Type: Article
Times cited : (17)

References (61)
  • 1
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  • 2
    • 0003455364 scopus 로고
    • Springer-Verlag, Berlin-Heidelberg
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    • (1994) Scent and Fragrancies , pp. 164
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  • 13
    • 0001369589 scopus 로고
    • (-)-trans-γ-Irone + (-)-cis-γ-irone (separated by prep. GC): [4b] C. Chapuis, R. Brauchli, Helv. Chim. Acta 1993, 76, 2070-2088.
    • (1993) Helv. Chim. Acta , vol.76 , pp. 2070-2088
    • Chapuis, C.1    Brauchli, R.2
  • 28
    • 0001140189 scopus 로고
    • Polyene cyclizations
    • (Eds.: B. M. Trost, I. Fleming) Pergamon Press, Oxford, New York, Seoul, Tokyo
    • [6a] J. K. Sutherland, "Polyene cyclizations" in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming) Pergamon Press, Oxford, New York, Seoul, Tokyo, 1991, vol. 3, p. 341-377.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 341-377
    • Sutherland, J.K.1
  • 34
  • 41
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    • [12b] F. W. Sum, L. Weiler, Tetrahedron 1981, 37, Supplement I, 303-317.
    • (1981) Tetrahedron , vol.37 , Issue.SUPPL. I , pp. 303-317
    • Sum, F.W.1    Weiler, L.2
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    • 0242276543 scopus 로고    scopus 로고
    • note
    • 5-Me = 1.68 ppm) revealed also the presence (ca. 15%) of the endocyclic olefin 7a.
  • 45
    • 0006453835 scopus 로고
    • The relative stereochemistry of compound 7 and derivatives can easily be assigned on the basis of the chemical shift values of the vinyl protons, see: [16a] J.-P. Pillot, G. Déléris, J. Dunoguès, R. Calas, J. Org. Chem. 1979, 44, 3397-3400.
    • (1979) J. Org. Chem. , vol.44 , pp. 3397-3400
    • Pillot, J.-P.1    Déléris, G.2    Dunoguès, J.3    Calas, R.4
  • 46
    • 0041540779 scopus 로고    scopus 로고
    • [16b] M. G. Organ, D. D. Winkle, J. Huffmann, J. Org. Chem. 1997, 62, 5254-5266). In cis-7 these two proton signals are separated farther than in trans-7 (δ = 4.67 and 4.85 ppm vs. δ = 4.76 and 4.85 ppm, respectively).
    • (1997) J. Org. Chem. , vol.62 , pp. 5254-5266
    • Organ, M.G.1    Winkle, D.D.2    Huffmann, J.3
  • 47
    • 0344694787 scopus 로고
    • and references cited therein
    • To this purpose, cyclizations promoted by "onio" species resemble those initiated by protonation of the terminal epoxide of a polyolefin; see: ref.[6a] and: [17a] R. J. Armstrong, L. Weiler, Can. J. Chem. 1986, 64, 584-596 and references cited therein.
    • (1986) Can. J. Chem. , vol.64 , pp. 584-596
    • Armstrong, R.J.1    Weiler, L.2
  • 54
    • 0242276542 scopus 로고    scopus 로고
    • note
    • 4 returned a cis/trans = 1:5 mixture of compound 21a.
  • 60
    • 0242308392 scopus 로고    scopus 로고
    • note
    • 2), ee = 97%.[3]
  • 61
    • 0242371342 scopus 로고    scopus 로고
    • note
    • 2), ee > 99%[2e].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.