Review Article

Unsaturated Sugars in Enantiospecific Synthesis of Natural Low-Molecular Bioregulators and Their Structural Analogues

A. G. Tolstikov1#  and G. A. Tolstikov2

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1Boreskov Institute of Catalysis, Siberian Division, Russian Academy of Sciences, 630090, Novosibirsk, pr. akademika Lavrent’eva 5, Novosibirsk, 630090, Russia;
2Vorozhtsov Institute of Organic Chemistry, Novosibirsk, Russia

Received: April 16, 2006; in final form: June 16, 2006

Abstract. The review of works of the authors devoted to the synthesis of low-molecular bioregulators with the use of unsaturated sugars is presented. The schemes of synthesis of insect pheromones and acetogenins and glycophosphingolipids on the basis of glycals are discussed. The pathways of synthesis of triterpene 2-deoxy-α-glycosides are shown. The synthesis of prostanoids from levoglucosenone is considered.

Key words: α-2-deoxyglycosides, glycols, levoglucosenone, glycophosphingolipids, pheromones, prostaglandin H2, triterpenoids

Russian Journal of Bioorganic Chemistry 2007, 33 (1): 3-23