PREPARATION OF CARBASUGARS FROM CARBOHYDRATES
Juan de la Cierva 3, 28806 Madrid, SPAIN
e-mail: clopez@iqog.csic.es
The term carbasugar is currently used to define structures in which the endocyclic oxygen atom in a carbohydrate has been substituted by a methylene group. In the past few years our group has been interested in the preparation of carbasugars from carbohydrates. To this aim, we have recently described two synthetic strategies based on radical cyclization of modified carbohydrates [1,2].
The first approach is based on a 6-endo-trigonal radical cyclization and the second features a 6-exo-digonal radical ring closure. The implementation of these methods have allowed the preparation seven different carbasugars and some derivatives thereof.
These studies have also given rise to a synthetic method which permits a one pot correlation between terminal alkynes and 1,2-diols [3].
References:
[1]. Gómez, A. M.; Danelón, G. O.; Valverde, S.; López, J. C. J. Org. Chem. 1998, 63, 9626-9627.
[2]. Gómez, A. M.; Danelón, G. O.; Moreno, E.; Valverde, S.; López, J. C. Chem. Commun., 1999, 175-176.
[3]. Gómez, A. M.; Company, M. D.; Valverde, S.; López, J. C. Organic Letters, 2002, 4, 383-386.