Models for the synthesis of pluramycin antibiotics. Rearrangement of mono-protected aminoglycal-substituted cyclohexadienediols

Journal of Carbohydrate Chemistry

Volumn 24, Issue 2, 2005, Pages 199-208

  Parker, Kathlyn A ^a,b   Su, Dai Shi ^a,c  

^a BROWN UNIVERSITY   (United States)

^b STONY BROOK UNIVERSITY   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Aminoglycal; Bis C glycoside; Dienolphenol; Pluramycin; Polarity; Quinol; Quinone; Rearrangement; Regiospecific; Umplong

Indexed keywords

EID: 27844596335     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1081/CAR-200059936     Document Type: Conference Paper

References (26)

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11. See also (e) Dubois, E.; Beau, J.M. Synthesis of C-glycopyranosyl compounds by a palladium-catalyzed coupling reaction of 1-tributylstannyl-D- glucals with organic halides. Carbohydr. Res. 1992, 228, 103;
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14. and (h) Sato, S.; Akiya, T.; Suzuki, T.; Onodera, J.I. Environmentally friendly C-glycosylation of phloroacetophenone with unprotected D-glucose using scandium(III) trifluoromethanesulfonate in aqueous media: key compounds for the synthesis of mono- and di-C-glucosylflavonoids. Carbohydr. Res. 2004, 339, 2611.
15. Although aryl C-aminoglycosides have been prepared by the direct glycosylation of the aromatic aglycone, indirect methods are used more frequently and in systems where the direct approach offers poor yields or other disadvantages. See: (a) Parker, K.A.; Ding, Q.J. Relative reactivities of amino glycosides and their synthetic equivalents in the C-glycosylation of aromatics. Synthesis of the psuedoaglycon (D-C-glycoside) of the benzanthrins. Tetrahedron 2000, 56, 10255;
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17. (c) Brimble, M.A.; Davey, R.M.; McLeod, M.D.; Murphy, M. C-Glycosylation of oxygenated naphthols with 3-dimethylamino-2,3,6-trideoxy-L-arabino- hexopyranose and 3-azido-2,3,6-trideoxy-D-arabino-hexopyranose. Aust. J. Chem. 2003, 56, 787;
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22. (a) Parker, K.A.; Coburn, C.A. Reductive aromatization of quinol ketals: A new synthesis of C-aryl glycosides. J. Am. Chem. Soc. 1991, 113, 8516;
23. (b) Parker, K.A.; Coburn, C.A.; Johnson, P.D.; Aristoff, P. Reductive aromatization of quinols. New convenient methods for the regiospecific synthesis of p-hydroxy C-aryl glycals. J. Org. Chem. 1992, 57, 5547;
24. (c) Parker, K.A.; Coburn, C.A.; Koh, Y.H. Reductive and non-reductive aromatization of quinol ketal glycals. Models for the preparation of C-aryl glycoside natural products. J. Org. Chem. 1995, 60, 2938;
25. (d) Parker, K.A.; Koh, Y.H. unpublished results.
26. Parker, K.A.; Su, D.S. previous paper in this issue.