Development of new synthetic methodologies for aminocyclitols

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2011
Ekmekçi, Zeynep
Aminocyclitols are cyclitols in which at least one of the hydroxyl groups is exchanged with an amino functional group. In turn, they constitute a wide group of natural products with interesting biological properties and are widely distributed throughout. In particular, antibiotics containing an aminocyclitol unit have stimulated the development of synthetic methodologies in the search for analogues with enhanced pharmacological profiles. In this study, three different methods were applied to synthesize diaminoconduritol derivative 202. In the first method, 1,2,3,6-tetraphthalic anhydrate (196), derived from Diels-Alder reaction between of maleic anhydride and 3-sulfolene, was used as a starting compound. Starting with the opening of anhydride group with trimethyl silylazide, tetrazolinone derivative 205 instead of bisamino cyclohexane derivative 201 was obtained. v In the second method, we started the synthesis of target compound 202 by the Birch reduction of benzene. Lactame 218 was synthesized as a key compound. Functionalization of lactame 218 was started with the cleavage of bond between nitrogen and carbonyl group in 218. At the end of the method, imidazole derivative 215 was obtained instead of target compound 202. Diaminoconduritol 242 was synthesized successfully by bishydrazide method. In this strategy, 1,2,3,6-tetraphthalic anhydrate (196) was used as a starting material. After conversion of bisurethane 223 to acylazide derivative 230, Curtius degradation and phtooxygenation reactions were used to introduce the amine and oxygen functionalities into the cyclohexene ring.

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Citation Formats
Z. Ekmekçi, “Development of new synthetic methodologies for aminocyclitols,” Ph.D. - Doctoral Program, Middle East Technical University, 2011.