Bile Acid-Piperazine Diamides: Novel Steroidal Templates in Syntheses of Supramolecular Hosts: Isomeric Pyridine-n-carboxy Containing Dimers and a Cholaphane

Jari Tamminen; Erkki Kolehmainen; Mervi Haapala; Juha Linnanto

doi:10.1055/s-2000-7113

Synthesis 2000; 2000(10): 1464-1468
DOI: 10.1055/s-2000-7113

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Bile Acid-Piperazine Diamides: Novel Steroidal Templates in Syntheses of Supramolecular Hosts: Isomeric Pyridine-n-carboxy Containing Dimers and a Cholaphane

Jari Tamminen^* , Erkki Kolehmainen, Mervi Haapala, Juha Linnanto

^*Department of Chemistry, University of Jyväskylä, P.O.B. 35, FIN-40351, Jyväskylä, Finland; Fax + 35 81 42 60 25 01; E-mail: jatata@cc.jyu.fi

Abstract

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Novel steroidal dimers: 3α,3′α-dihydroxy-5β-cholan-24-oic acid piperazine diamide 3, its 3α,3′α-bis(trifluoroacetoxy) protected derivative 2, and 3α,3′α-bis(pyridine-n-carboxy, n = 2-4) derivatives 4-6 and their Ag⁺-complexes have been prepared. A novel cholaphane 7 has also been synthesized from 3 by cyclization with terephthalic acid by Yamaguchi method. Products were characterized by ¹³C and ¹⁵N NMR chemical shifts and MALDI-TOF MS. In addition, MO-calculations (PM3) for 3 and 7 were performed.

steroids - macrocycles - molecular recognition - Ag⁺-complexes - NMR

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