The First Example of Cascade Synthesis of Alkaloid-like Subunit Incorporated into Crown Ethers

Irina G. Ovchinnikova,^@1 Olga V. Fedorova, Eugenia G. Matochkina, Mikhail I. Kodess, Andrey A. Tumashov, Pavel A. Slepukhin, Gennady L. Rusinov, and Valery N. Charushin^@2

I.Y. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Science, 620041 Ekaterinburg, GSP-147, Russia

^@1Corresponding author E-mail: iov@ios.uran.ru

^@2Corresponding author E-mail: charushin@ios.uran.ru

DOI: 10.6060/mhc2010.2-3.108

A new type of template-assisted cyclization was found to occur in the course of nucleophilic reactions on chalcone podands, thus resulting in the formation of rather new complex polycyclic compounds. The structure of 25-methyl-
23,29-diphenyl-8,11,14-trioxa-24-azahexa-cyclo[20.8.0.02,7.015,20.021,26.025,30]triaconta-2,4,6,15(20),16,18,23,28-octaene-27-one was established by means of IR (DRA), 1H and 13С NMR spectroscopy, as well as the X-ray crystallography. Polycyclic crownophane with the core of 2-azabicyclo[2.2.2]oct-2-ene can be regarded as synthetic analogues of Daphniphyllum alkaloids.

Keywords: Template synthesis, chalcone podands, crown ethers, alkaloids, cascade reactions.

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