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Volumn 71, Issue 16, 2006, Pages 6273-6276

Synthesis of pentahydroxy indolizidine alkaloids using ring closing metathesis: Attempts to find the correct structure of uniflorine A

Author keywords

[No Author keywords available]

Indexed keywords

D-GLUCOSE; DIHYDROXYLATION; NITROGEN FUNCTIONALITY; RING CLOSING METATHESIS; UNIFLORINE A;

EID: 33746911198     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060823s     Document Type: Article
Times cited : (46)

References (66)
  • 10
    • 0034246704 scopus 로고    scopus 로고
    • (i) Larry, Y. Chem. Rev. 2000, 100, 2963-3008.
    • (2000) Chem. Rev. , vol.100 , pp. 2963-3008
    • Larry, Y.1
  • 27
    • 0035232404 scopus 로고    scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • (b) Howard, A. S.; Michael, J. P. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 2001; Vol. 55, pp 91-258.
    • (2001) The Alkaloids , vol.55 , pp. 91-258
    • Howard, A.S.1    Michael, J.P.2
  • 29
    • 0008881075 scopus 로고    scopus 로고
    • Stuetz, A., Ed.; Wiley-VCH Verlag GmbH: Weinheim, Germany
    • For selected syntheses see the following: (a) Tyler, P. C.; Winchester, B. G. In Iminosugars as Glycosidase Inhibitors; Stuetz, A., Ed.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 1999; pp 125-156.
    • (1999) Iminosugars As Glycosidase Inhibitors , pp. 125-156
    • Tyler, P.C.1    Winchester, B.G.2
  • 50
    • 0035056125 scopus 로고    scopus 로고
    • These results are consistent with our earlier studies on the 1,3-addition of methyl-and allyl-magnesium bromide as well as silyl ketene acetal of ethyl acetate to nitrone 3, in the presence of TMSOTf (1 equiv) at -78 °C in THF, that afforded a good diastereoselectivity in the favor of D-gluco isomer (∼de 75%). (a) Saha, N. N.; Desai, V. N.; Dhavale, D. D. Tetrahedron 2001, 57, 39-46.
    • (2001) Tetrahedron , vol.57 , pp. 39-46
    • Saha, N.N.1    Desai, V.N.2    Dhavale, D.D.3
  • 54
    • 0030460450 scopus 로고    scopus 로고
    • For the application of the ring closing metathesis reaction to the synthesis of 2,5-dihydropyrrolidines from dienes see (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2376-2378
    • Huwe, C.M.1    Velder, J.2    Blechert, S.3
  • 60
    • 0042250061 scopus 로고
    • For reviews on dihydroxylation see (a) Masaya, S.; Yoshihiko, I. Chem. Rev. 1992, 92, 857-871.
    • (1992) Chem. Rev. , vol.92 , pp. 857-871
    • Masaya, S.1    Yoshihiko, I.2
  • 65
    • 18744402201 scopus 로고    scopus 로고
    • In this experiment, weak nOe was also observed between the H-6 and the H-5 in 9a and 9b. Similar observation was also noticed in pyrrolidine derivatives; see Kim, J. H.; Curtis-Long, M. J.; Seo, W. D.; Ryu, Y. B.; Yang, M. S.; Park K. H. J. Org. Chem. 2005, 70, 4082-4087.
    • (2005) J. Org. Chem. , vol.70 , pp. 4082-4087
    • Kim, J.H.1    Curtis-Long, M.J.2    Seo, W.D.3    Ryu, Y.B.4    Yang, M.S.5    Park, K.H.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.