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Synlett 2003(5): 0598-0608
DOI: 10.1055/s-2003-38344
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Molecular Signal Transduction by Conformational Transmission

Rolf Krauss, Ulrich Koert*
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35032 Marburg, Germany
Fax: +49(6421)2825677; e-Mail: koert@chemie.uni-marburg.de;
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Publication History

Received 18 June 2002
Publication Date:
28 March 2003 (online)

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Abstract

2,3,6,7-Tetrasubstituted cis-anti-cis perhydroanthra-cenes and cis-decalines are suitable transducers for molecular signals via conformational transmission. Repeated use of a Lewis-acid catalyzed Diels-Alder reaction led to the stereoselective construction of the perhydroanthracene and decalin target molecules. A covalently induced triple ring flip of the perhydroanthacene system was achieved by the formation of a bisacetal. A chelation induced conformational switch was possible with bipyridine receptor groups in positions 6 and 7 and Zn(II) as the incoming signal. By attaching pyrene effectors in positions 2 and 3 the ability of the device to transduce a molecular signal from the receptor via the biconfor­mational transducer to the effector leading to an outcoming photosignal was proven.

Key words

conformational analysis - molecular switch - perhydroanthracene - signal transduction - stereoselective synthesis

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