A General C-Glycosidation Procedure via Anomeric Oxygen to Carbon Rearrangements of Tetrahydropyranyl Ether Derivatives

Synlett

Volumn 1997, Issue 9, 1997, Pages 1055-1056

  Buffet, Marianne F ^a   Dixon, Darren J ^a   Edwards, Gavin L ^a,b   Ley, Steven V ^a   Tate, Edward ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001923328     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1531     Document Type: Article

References (9)

1. For examples see: i) D. E. Levy and C. Tang, 'The Chemistry of C-Glycosides' Pergamon, 1995. ii) Postema, M. H. D. Tetrahedron, 1992, 48, 8545.
2. For examples see: i) D. E. Levy and C. Tang, 'The Chemistry of C-Glycosides' Pergamon, 1995. ii) Postema, M. H. D. Tetrahedron, 1992, 48, 8545.
3. Menicagli, R.; Malanga, C.; Dell'Innocenti, M.; Lardicci, L. J. Org. Chem., 1987, 52, 5700.
4. For examples of aryl O- to C- anomeric rearrangements see: i) Ramesh, N. G.; Balasubramanian, K. K. Tetrahedron Lett., 1992, 33, 3061. ii) Casiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Tetrahedron Lett., 1988, 29, 3323. iii) Casiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Carbohydrate Res., 1989, 191, 243.
5. For examples of aryl O- to C- anomeric rearrangements see: i) Ramesh, N. G.; Balasubramanian, K. K. Tetrahedron Lett., 1992, 33, 3061. ii) Casiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Tetrahedron Lett., 1988, 29, 3323. iii) Casiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Carbohydrate Res., 1989, 191, 243.
6. For examples of aryl O- to C- anomeric rearrangements see: i) Ramesh, N. G.; Balasubramanian, K. K. Tetrahedron Lett., 1992, 33, 3061. ii) Casiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Tetrahedron Lett., 1988, 29, 3323. iii) Casiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Carbohydrate Res., 1989, 191, 243.
7. An aliphatic O- to C- rearrangement has been suggested to rationalise C-glycoside products in the treatment of glycals with alkenols: Herscovici, J.; Delatre, S.; Antonakis, K. J. Org. Chem., 1987, 52, 5691.
8. All starting materials were readily prepared by the acid catalysed addition of an appropriate alkenol to a 3,4-dihydro-2H-pyran derivative or by acylation of a suitable lactol with the requisite acid chloride.
9. For a related example see: Herscovici, J.; Boumaiza, L.; Antonakis, K. J. Org. Chem., 1992, 57, 2476.