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Volumn , Issue 4, 2009, Pages 573-576

A ruthenium-mediated asymmetric hydrogenation approach to the synthesis of discodermolide subunits

Author keywords

Asymmetric catalysis; Hydrogenation; Natural products; Ruthenium; Total synthesis

Indexed keywords


EID: 62249114185     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087917     Document Type: Article
Times cited : (7)

References (49)
  • 1
    • 0025160288 scopus 로고    scopus 로고
    • Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. J. Org. Chem. 1990, 55, 4912; correction: J. Org. Chem. 1991, 56, 1346.
    • (a) Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. J. Org. Chem. 1990, 55, 4912; correction: J. Org. Chem. 1991, 56, 1346.
  • 13
    • 0038392453 scopus 로고    scopus 로고
    • For a review of the total syntheses prior to 2003
    • (a) For a review of the total syntheses prior to 2003: Paterson, I.; Florence, G. J. Eur. J. Org. Chem. 2003, 2193.
    • (2003) Eur. J. Org. Chem , pp. 2193
    • Paterson, I.1    Florence, G.J.2
  • 14
    • 36549038147 scopus 로고    scopus 로고
    • For a recent review on syntheses, construction and biological evaluation of analogues
    • (b) For a recent review on syntheses, construction and biological evaluation of analogues: Smith, A. B. III.; Freeze, B. S. Tetrahedron 2008, 64, 261.
    • (2008) Tetrahedron , vol.64 , pp. 261
    • Smith III, A.B.1    Freeze, B.S.2
  • 15
    • 41749125906 scopus 로고    scopus 로고
    • For a recent review on total syntheses of discodermolide and dictyostatin
    • (c) For a recent review on total syntheses of discodermolide and dictyostatin: Florence, G. J.; Gardner, N. M.; Paterson, I. Nat. Prod. Rep. 2008, 25, 342.
    • (2008) Nat. Prod. Rep , vol.25 , pp. 342
    • Florence, G.J.1    Gardner, N.M.2    Paterson, I.3
  • 16
    • 62249141906 scopus 로고    scopus 로고
    • For references to synthetic approaches to discodermolide, see ref. 6b
    • (d) For references to synthetic approaches to discodermolide, see ref. 6b.
  • 20
    • 0000888244 scopus 로고    scopus 로고
    • Synthetic approaches to discodermolide involving C1-C7 lactone subunit: (a) Miyazawa, M.; Oonuma, S.; Maruyama, K.; Miyashita, M. Chem. Lett. 1997, 26, 1191.
    • Synthetic approaches to discodermolide involving C1-C7 lactone subunit: (a) Miyazawa, M.; Oonuma, S.; Maruyama, K.; Miyashita, M. Chem. Lett. 1997, 26, 1191.
  • 24
    • 0011779578 scopus 로고    scopus 로고
    • For reviews on Ru-catalyzed asymmetric hydrogenation, see: a, 2nd ed, Ojima, I, Ed, Wiley-VCH: New York
    • For reviews on Ru-catalyzed asymmetric hydrogenation, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000, 1.
    • (2000) Catalytic Asymmetric Synthesis , pp. 1
    • Ohkuma, T.1    Kitamura, M.2    Noyori, R.3
  • 28
    • 62249166013 scopus 로고    scopus 로고
    • Duprat de Paule, S, Champion, N, Ratovelomanana-Vidal, V, Genet, J.-P, Dellis, P
    • (a) Duprat de Paule, S.; Champion, N.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P. .
  • 42
    • 62249147102 scopus 로고    scopus 로고
    • +.
    • +.
  • 43
    • 62249212935 scopus 로고    scopus 로고
    • Spectroscopic Data for Compound 10 [α]D 25 +5.5 (c 1.05, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 6.23 (d, J, 9.8 Hz, 1 H, 4.28 (dd, J, 6.8, 4.1 Hz, 1 H, 2.52-2.67 (m, 2 H, 1.47 (s, 9 H, 1.13 (d, J, 7.2 Hz, 3 H, 1.10 (s, 18 H, 1.04-1.13 (s, 3 H, 1.07 (d, J, 7.0 Hz, 3 H, 13C NMR (75 MHz, CDCl3, δ, 172.7, 140.8, 88.8, 80.7, 75.1, 46.9, 42.0, 28.2, 18.2, 15.5, 13.1, 9.4. IR (film, 1733, 1460, 1255, 882 cm-1. MS DCI/NH3, m/z, 529 [M, H, Anal. Calcd for C21H40Br 2O3Si: C, 47.73; H, 7.63. Found: C, 47.81; H, 7.51
    • 3Si: C, 47.73; H, 7.63. Found: C, 47.81; H, 7.51.
  • 49
    • 62249143737 scopus 로고    scopus 로고
    • +.
    • +.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.