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Volumn 6, Issue 4, 2008, Pages 703-711

Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi- lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi- homocastanospermine from a d-glucose-derived aziridine carboxylate, and study of their glycosidase inhibitory activities

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CARBOXYLATION; CHEMICAL REACTIONS; ESTERS; GLUCOSE; ORGANIC COMPOUNDS;

EID: 38949179531     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b712753g     Document Type: Article
Times cited : (46)

References (117)
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    • Denmark, S.E.1    Herbert, B.2
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    • For recent reports on the synthesis of swainsonine, lentiginosine and their analogues, see: -8629
    • A. E. Nemr Tetrahedron 2000 56 8579 8629
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    • Nemr, A.E.1
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    • For recent reviews on glycosidase mechanisms, see: -8
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    • A minor amount of ring-opened product with Z-geometry is observed (<6%). The major isomer was separated by flash chromatography and characterized using 1H and 13C NMR spectra; however, due to the close Rf values we could not separate the Z-isomer in a pure form This observation also supports the aziridine ring opening in 9 occurring exclusively at the C6 position -482
    • O. L. Lopez J. G. Fernandez-Bolanos V. H. Lillelund M. Bols Org. Biomol. Chem. 2003 1 478 482
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    • The product after hydrogenation was a mixture of δ-amino saturated ester (80%) and cyclized δ-lactam (∼20%) as indicated by the 1H NMR spectra. The mixture was therefore subjected to sodium acetate in methanol to afford δ-lactam as the only product Our assumption was supported by the fact that when aziridine carboxylate 1 was subjected to hydrogenation, under conditions identical to those for 9, an N/O-debenzylated aziridine ester was obtained, indicating high stability of the aziridine ring in 1 to the hydrogenation. For mechanistic aspects in hydrogenation, see: -458
    • H. Yakawa S. Kimura Nippon Kagaku Zasshi 1955 78 454 458
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.