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Pure Appl. Chem. 76(5), 1025-1032, 2004

Pure and Applied Chemistry

Vol. 76, Issue 5

Synthesis of naturally occurring o-heterocyclic compounds of biological activity

S. Antus, K. Gul�csi, L. Juh�sz, L. Kiss, and T. Kurt�n

Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen,
P.O. Box 20, Hungary

Abstract: The total synthesis of (–)-cabenegrin A-I was achieved via (–)-6aR,11aR maackiain, which was obtained by optical resolution of racemic maackiain using S-(–)-alpha-methylbenzyl isocyanate. The synthesis of rac-maackiain was performed both with the Heck oxyarylation of 7-benzyloxy-2H-chromene and the BF3OEt2 mediated ring closure of isoflavan-4-ol derivatives, the latter of which provided much higher yields. The first enantioselective synthesis of trans-6aS,11aR-pterocarpan and its conversion to cis-6aS,11aS -ptarocarpan was also presented starting from racemic 2'-benzyloxyflavanone. Their stereochemistry was deduced by circular dichroism (CD) as well as by X-ray analysis of the ketal intermediate.

*Lecture presented at the Polish-Austrian-German-Hungarian-Italian Joint Meeting on Medicinal Chemistry, Krak�w, Poland, 15-18 October 2003. Other presentations are published in this issue, pp. 907 -1032.


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