Pure Appl. Chem., 2005, Vol. 77, No. 7, pp. 1173-1181
doi:10.1351/pac200577071173
Carbohydrates as versatile platforms in the construction of small compound libraries*
Mattie S. M. Timmer, Steven H. L. Verhelst, Gijsbert M. Grotenbreg, Mark Overhand, and Herman S. Overkleeft
Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2300 RA Leiden, The Netherlands
Abstract:
This paper presents our recent results concerning the use of carbohydrates as cheap, chiral, and enantiopure starting materials in the construction of a variety of densely functionalized molecules. The compatibility of ring-closing metathesis with standard carbohydrate chemistry is demonstrated in the synthesis of new stereoisomers of deoxystreptamine and neamine–important building blocks for the generation of synthetic aminoglycosides with potential antibacterial activity. Ring-closing metathesis is also a key step in the rapid synthesis of new indolizidines and quinolizidines, and in a new solid-phase assisted carbohydrate-based combinatorial scaffold strategy. Further, some of our latest results in the conformational analysis of sugar amino acid-based peptide mimetics and in the development of a novel Ugi-type three-component reaction of sugar-derived azido-aldehydes are discussed.
Keywords: aminoglycosides; antibacterial; carbohydrates; combinatorial platforms; deoxystreptamine; indolizidines; neamine; quinolizidines; ring-closing metathesis; Ugi 3-CR.
*An issue of reviews and research papers based on lectures presented at the 15th International Conference on Organic Synthesis (ICOS-15), held in Nagoya, Japan, 1-6 August 2004, on the theme of organic synthesis. Other presentations are published in this issue, pp. 1087-1296.
All articles from the 15th International Conference on Organic Synthesis (ICOS-15), Nagoya, Japan, 1–6 August 2004.