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Volumn 46, Issue 17, 2005, Pages 3015-3019

De novo synthesis of galacto-sugar δ-lactones via a catalytic osmium/palladium/osmium reaction sequence

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CARBOHYDRATE DERIVATIVE; GALACTOSE; LACTONE DERIVATIVE; MEQUINOL; OSMIUM; PALLADIUM;

EID: 15944404632     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.029     Document Type: Article
Times cited : (31)

References (26)
  • 3
    • 1642407159 scopus 로고    scopus 로고
    • B.O. Fraser-Reid K. Tatsuta J. Thiem Springer Berlin
    • P. Vogel B.O. Fraser-Reid K. Tatsuta J. Thiem Glycoscience Vol. 2 2001 Springer Berlin 1023 1174
    • (2001) Glycoscience , vol.2 , pp. 1023-1174
    • Vogel, P.1
  • 13
  • 14
    • 0141954268 scopus 로고    scopus 로고
    • For related Achmatowicz approach to oligosaccharides see: R.S. Babu, and G.A. O'Doherty J. Am. Chem. Soc. 125 2003 12406 12407
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12406-12407
    • Babu, R.S.1    O'Doherty, G.A.2
  • 19
    • 85030814621 scopus 로고    scopus 로고
    • note
    • We have found that this reaction works for various phenols, however, simple alcohols (e.g., BnOH) did not participate in this reaction
  • 20
    • 85030816129 scopus 로고    scopus 로고
    • Recently we have found that when the Sharpless reagent was used in a matched fashion on diols 5a / c, tetrols were obtained in both excellent diastereoselectivity and enantioselectivity, see: Ref. 4
    • Recently we have found that when the Sharpless reagent was used in a matched fashion on diols 5a / c, tetrols were obtained in both excellent diastereoselectivity and enantioselectivity, see: Ref. 4
  • 22
    • 0027233896 scopus 로고
    • For a discussion of the use of the Sharpless AD-mix reagent in a matched/mismatched case see: Ref. 4 and K. Morikawa, and K.B. Sharpless Tetrahedron Lett. 34 1993 5575 5578
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5575-5578
    • Morikawa, K.1    Sharpless, K.B.2
  • 24
    • 85030814027 scopus 로고    scopus 로고
    • The overall sequence requires fewer steps (five vs eight) to a galacto-δ-lactone and occurs in a greater overall yield (40% vs 14%) than a related iterative aldol approach, see: Ref. 3e
    • The overall sequence requires fewer steps (five vs eight) to a galacto-δ-lactone and occurs in a greater overall yield (40% vs 14%) than a related iterative aldol approach, see: Ref. 3e
  • 25
    • 85030810411 scopus 로고    scopus 로고
    • note
    • 4,5 = 1.4 Hz)
  • 26
    • 85030815939 scopus 로고    scopus 로고
    • note
    • As a representative example of this approach we have included experimental details and spectral data for the conversion of 6a to 10a


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