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Synlett 2003(5): 0598-0608
DOI: 10.1055/s-2003-38344
DOI: 10.1055/s-2003-38344
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York
Molecular Signal Transduction by Conformational Transmission
Further Information
Received
18 June 2002
Publication Date:
28 March 2003 (online)
Publication History
Publication Date:
28 March 2003 (online)
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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