Novel Deep Cavity Calix[4]pyrroles Derived from Steroidal Ketones |
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| Authors: | Mykhaylo Dukh Pavel Drašar Ivan Černý VladimÍr Pouzar James A Shriver VladimÍr Král |
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| Institution: | 1. Institute of Organic Chemistry and Biochemistry AS CR , Flemingovo 2, Praha 6 , 166 10 , Czech Republic;2. Institute of Chemical Technology , Technická 5, Praha 6 , 166 28 , Czech Republic;3. Institute of Organic Chemistry and Biochemistry AS CR , Flemingovo 2, Praha 6 , 166 10 , Czech Republic;4. Department of Organic Chemistry and Biochemistry, Institute for Callular and Molecular Biology , University of Texas , at Austin, Austin , TX , 78712-1167 , USA;5. Institute of Chemical Technology , Technická 5, Praha 6 , 166 28 , Czech Republic |
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| Abstract: | Novel steroidal calix4]pyrroles were prepared in excellent yields from commercially available cholic acid derivatives using an efficient synthetic sequence. Once in hand, it was found that these calix4]pyrroles exist in the form of four different configurational isomers. Separation of these isomers was achieved readily using normal phase HPLC techniques. Once purified, the steroidal calix4]pyrroles were screened via -FABMS analyses to judge their utility in effecting the enantioselective recognition of appropriate organic anions. Results that provided support for antipodal R > S selectivity were obtained in the case of both tartaric acid and mandelic acid. Direct extraction studies were then carried out and these confirmed the pattern of R > S selectivity observed by -FABMS. |
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