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Volumn 8, Issue 19, 2006, Pages 4339-4342

A stereoselective synthesis of digitoxin and digitoxigen mono- and bisdigitoxoside from digitoxigenin via a palladium-catalyzed glycosylation

Author keywords

[No Author keywords available]

Indexed keywords

DIGITOXIGEN BISDIGITOXOSIDE; DIGITOXIGENIN; DIGITOXIN; DRUG DERIVATIVE; PALLADIUM;

EID: 33749022998     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061683b     Document Type: Article
Times cited : (100)

References (52)
  • 8
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    • note
    • -1).
  • 9
    • 33748993918 scopus 로고
    • Cardiac Glycosides, Part 1: Experimental Pharmacology
    • Springer-Verlag: Berlin; New York
    • Greeff, K. Cardiac Glycosides, Part 1: Experimental Pharmacology. In Handbook of Experimental Pharmacology; Springer-Verlag: Berlin; New York, 1981; Vol. 56.
    • (1981) Handbook of Experimental Pharmacology , vol.56
    • Greeff, K.1
  • 18
    • 0344709508 scopus 로고
    • The attempts at the selective hydrolysis of digitoxin (1) to form digoxose (3) have been futile; only the monosaccharide digitoxose was isolated. Surprisingly, 3 can be isolated from the dried twigs of Orthenthera viminea; see: Tiwari, K. N.; Khare, N. K.; Khare, A.; Khare, M. P. Carbohydr. Res. 1984, 129, 179-187.
    • (1984) Carbohydr. Res. , vol.129 , pp. 179-187
    • Tiwari, K.N.1    Khare, N.K.2    Khare, A.3    Khare, M.P.4
  • 24
    • 33749014346 scopus 로고    scopus 로고
    • see ref 7
    • In both the Wiesner and McDonald syntheses of digitoxin at least one of the three glycosidic bonds was assembled with poor stereoselectivity; see ref 7.
  • 29
    • 0038341685 scopus 로고    scopus 로고
    • In contrast, McDonald is able to use his methodology to prepare an all-α-analogue of digitoxin with high stereocontrol; see: McDonald, F. E.; Wu, M. Org. Lett. 2002, 4, 3979-3981.
    • (2002) Org. Lett. , vol.4 , pp. 3979-3981
    • McDonald, F.E.1    Wu, M.2
  • 33
    • 1642342224 scopus 로고    scopus 로고
    • For its application in the de novo synthesis of α-linked 1,4- and 1,6-oligosaccharides, see: (d) Babu, R. S.; Zhou, M.; O'Doherty, G. A. J. Am. Chem. Soc. 2004, 126, 3428-3429.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 3428-3429
    • Babu, R.S.1    Zhou, M.2    O'Doherty, G.A.3
  • 39
    • 33947094130 scopus 로고
    • 3 is necessary to avoid 1,4-reduction products. For the Luche reduction, see: (a) Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226-2227.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 2226-2227
    • Luche, J.L.1
  • 46
    • 85008566407 scopus 로고
    • Mono- and bis-digtoxosides has been prepared by gradual degradation of digitoxin, see: (a) Satoh, D., Aoyama, K. Chem. Pharm. Bull. 1970, 18, 94-98.
    • (1970) Chem. Pharm. Bull. , vol.18 , pp. 94-98
    • Satoh, D.1    Aoyama, K.2
  • 48
    • 33749031767 scopus 로고    scopus 로고
    • note
    • The nomenclature of compounds 20 and 26 was used according to ref 18.
  • 49
    • 84990156542 scopus 로고
    • Acetate protecting group was demonstrated to provide significant stabilization effect for the acid-sensitive glycosides. (a) Kunz, H.; Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 1697-1699.
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 1697-1699
    • Kunz, H.1    Unverzagt, C.2
  • 52
    • 33748999213 scopus 로고    scopus 로고
    • note
    • Digitoxin purchased from Acros was used to do the comparison.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.