Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of lactols

Synlett

Volumn , Issue 10, 1998, Pages 1091-1092

  Buffet, Marianne F ^a   Dixon, Darren J ^a   Ley, Steven V ^a   Tate, Edward W ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002282303     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1866     Document Type: Article

References (11)

1. For excellent reviews see: i) Levy, D.; Tang, C. The Chemistry of C-Glycosides, Pergamon, 1995;
2. ii) Postema, M. H. D. Tetrahedron, 1992, 48, 8545, and references cited therein.
3. Buffet, M. F.; Dixon, D. J.; Edwards, G. L.; Ley, S. V.; Tate, E. W. Synlett, 1997, 1055.
4. Menicagli, R.; Malanga, C.; Dell'Innocenti, M.; Lardicci, L. J. Org. Chem., 1987, 52, 5700.
5. For examples of aryl O- to C- anomeric rearrangements see: i) Ramesh, N. G.; Balasubramanian, K. K. Tetrahedron Lett., 1992, 33, 3061;
6. ii) Casiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Tetrahedron Lett., 1988, 29, 3323;
7. iii) Casiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Carbohydrate Res., 1989, 191, 243.
8. For examples see: i) Herscovici, J.; Delatre, S.; Antonakis, K. J. Org. Chem., 1987, 52, 5691;
9. ii) Mikami, K.; Kishino, H.; Tetrahedron Lett., 1996, 37, 3705.
10. Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 250.
11. 3). The trans geometry of 12 was confirmed by nOe experiments.