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Volumn 48, Issue 36, 2007, Pages 6267-6270

Total synthesis of (+)-galanthamine starting from d-glucose

Author keywords

Chiral synthesis; Claisen rearrangement; Galanthamine

Indexed keywords

2 NITROPHENOL; AMIDE; BROMIDE ION; BROMONIUM ION; CARBON; CYCLOHEXENE DERIVATIVE; DIBENZOFURAN; ETHER DERIVATIVE; GALANTAMINE; GLUCOSE; PHENOL DERIVATIVE; PLANT EXTRACT; QUARTERNARY CARBON; UNCLASSIFIED DRUG;

EID: 34547700961     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.042     Document Type: Article
Times cited : (59)

References (51)
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  • 4
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    • For comprehensive reviews on biological activities and synthetic studies of galanthamine-type Amaryllidaceae alkaloids, see:. Brossi A. (Ed), Academic Press, New York, NY
    • For comprehensive reviews on biological activities and synthetic studies of galanthamine-type Amaryllidaceae alkaloids, see:. Martin S.F. In: Brossi A. (Ed). The Alkaloids Vol. 30 (1987), Academic Press, New York, NY 251-376
    • (1987) The Alkaloids , vol.30 , pp. 251-376
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    • For chiral total syntheses of (+)- and (-)-galanthamine, see:
    • For chiral total syntheses of (+)- and (-)-galanthamine, see:. Tomioka K., Shimizu K., Yamada S.-i., and Koga K. Heterocycles 6 (1977) 1752-1756
    • (1977) Heterocycles , vol.6 , pp. 1752-1756
    • Tomioka, K.1    Shimizu, K.2    Yamada, S.-i.3    Koga, K.4
  • 24
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    • For preparation of (-)-galanthamine via spontaneous resolution of racemic narwedine, see:
    • For preparation of (-)-galanthamine via spontaneous resolution of racemic narwedine, see:. Shieh W.-C., and Carlson J.A. J. Org. Chem. 59 (1994) 5463-5465
    • (1994) J. Org. Chem. , vol.59 , pp. 5463-5465
    • Shieh, W.-C.1    Carlson, J.A.2
  • 30
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    • For utilization of Claisen rearragement in the synthesis of related alkaloids, see:
    • For utilization of Claisen rearragement in the synthesis of related alkaloids, see:. Keck G.E., and Webb II R.R. J. Org. Chem. 47 (1982) 1302-1309
    • (1982) J. Org. Chem. , vol.47 , pp. 1302-1309
    • Keck, G.E.1    Webb II, R.R.2
  • 35
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    • see also Ref. 9
    • Mulzer J., and Trauner D. Chirality 11 (1999) 475-482 see also Ref. 9
    • (1999) Chirality , vol.11 , pp. 475-482
    • Mulzer, J.1    Trauner, D.2
  • 41
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    • note
    • 13C NMR, IR, and mass spectrometric and/or elemental analyses.
  • 46
    • 34547659815 scopus 로고    scopus 로고
    • note
    • +, 287.1521.
  • 47
    • 34547683198 scopus 로고    scopus 로고
    • note
    • When propionic acid was employed as the acid in the Johnson-Claisen rearrangement of 4, the yield of 3 was found to be low (less than 25%) and the formation of significant amount of unidentified by-products was observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.