Synthesis of bergenin-related natural products by way of an intramolecular C-glycosylation reaction

Tetrahedron Asymmetry

Volumn 11, Issue 2, 2000, Pages 409-412

  Rousseau, Cyril ^a   Martin, Olivier R ^a  

^a Université d'Orléans   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BERGENIN; GLUCOPYRANOSIDE; NATURAL PRODUCT;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; PRIORITY JOURNAL;

EID: 0034635637     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00484-X     Document Type: Article

References (22)

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8. Martin, O. R.; Deshpande, P. P., unpublished results.
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12. For other examples of O-pentenyl orthoesters, see: (a) Roberts, C.; Madsen, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 117, 1546.
13. For other examples of O-pentenyl orthoesters, see: (b) Allen, J. G.; Fraser-Reid, B. J. Am. Chem. Soc. 1999, 121, 468.
14. (a) Ogawa, T.; Beppu, K.; Nakabayashi, S. Carbohydr. Res. 1981, 93, C6.
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16. Winstein, S.; Buckles, R. E. J. Am. Chem. Soc. 1942, 64, 2780. For its use in O-glycosylation reactions, see Ref. 10.
17. The internal C-arylation of a 2-O-benzyl glucopyranosyl chloride gave exclusively the α-linked (cis-fused) product: Verlhac, P.; Leteux, C.; Toupet, L.; Veyrières, A. Carbohydr. Res. 1996, 291, 11.
18. Partial iodination of the ring occurred in the course of the internal C-arylation of the 2-O-(3,5-dimethoxybenzyl) derivative of 8 using IDCP.
19. Carlsen, P. J. H.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
20. 13C NMR (62.9 MHz): δ 20.75 (3C), 56.28, 60.84 (C-6), 61.02, 61.91, 65.85, 68.09, 73.11, 73.54, 108.81 (ArCH), 119.97, 122.89, 147.46, 150.76, 154.8, 162.5, 168.75, 169.9, 170.53.
21. 3OD): δ 57.2, 61.43, 61.98, 62.54, 63.12, 69.58, 73.51, 80.87, 81.62, 109.94, 121.82, 126.07, 149.41, 152.93, 156.49, 166.01.
22. 3 signal.