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Paper | Regular issue | Vol 45, No. 2, 1997, pp.287-298
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7651
Conformational Analysis of Tetrahydrofurofuran Lignans: Sesamolin

Gerda Lutz, Otmar Hofer,* Günter Brader, and Christoph Kratky

*Institute of Organic Chemistry, University of Vienna, Währingerstrasse 38, A-1090 Vienna, Austria

Abstract

The stereochemisty of sesamolin (1), an aryl-aryloxy-tetrahydrofurofuran derivative comprising a main component of the lignans isolated from Sesamum indicum, was investigated. the favoured conformation was determined using several methods of conformational analysis: nuclear Overhauser effect (NOE), lanthanide induced shifts (1H-LIS), molecular mechanics (force-field) calculations (FF), and X-ray crystal structure determination. The conformation was found to be deviate from the more common analoguous diaryltetrahydrofurofuran derivatives. The reason is the anomeric effect of the cyclic acetal favouring a pseudo-axial position of the aryloxy substituent.