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■ Synthesis of Polycylic Systems via Diels-Alder Reactions of Sugar Derived Dienes

P. Areces Bravo,* M. C. Pozo Carrero, E. Román Galán, and J. A. Serrano Blázquez

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Extremadura, 06071 Badajoz, Spain

Abstract

Several Diels-Alder reactions of sugar derived dienes (2Z, 4E)-1,3,6-triacetoxyhexa-2,4-diene (2) and (2Z, 4E)-1,3-diacetoxy-6-cyclohexylamino-hexa-2,4-diene (3) with a number of electron-deficient dienophiles were carried out in a completely stereoselective manner to give the corresponding cycloadducts or cascade reaction products. Subsequent chemical transformations yielded highly functionalized polycyclic systems having a controlled stereochemistry. The new compounds described in here keep the all-cis configuration at their centers.