A Ramberg-Baecklund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids

Article abstract of DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Baecklund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Baecklund rearrangement is also reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.