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Issue 31, 2018
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Stereoselective synthesis of enantiomerically pure bowl-shaped hydroxytribenzotriquinacenes

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Abstract

Enzyme-catalysed hydrolysis of the inherently chiral aryl acetate rac-11 bearing the bowl-shaped tribenzotriquinacene (TBTQ) core enables the stereoselective synthesis of the enantiomerically pure (M)-2-hydroxytribenzotriquinacene (M)-12. Starting from rac-11, for which two independent routes are described, the use of immobilised lipase CAL-A in buffered biphasic solution at pH 7 led to the TBTQ-phenol (M)-12 in 33% yield and with >99% ee on a preparative scale. Extended enzyme screening revealed that the use of CAL-B gives the same enantioselectivity. Furthermore, the chiroptical properties of the enantiomerically pure TBTQ-acetates (M)-11 and (P)-11, TBTQ-phenols (M)-12 and (P)-12 and the corresponding 2-hydroxy-3-iodotribenzotriquinacenes (M)-13 and (P)-13 are reported.

Graphical abstract: Stereoselective synthesis of enantiomerically pure bowl-shaped hydroxytribenzotriquinacenes

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Publication details

The article was received on 15 Jun 2018, accepted on 17 Jul 2018 and first published on 17 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01425F
Citation: Org. Biomol. Chem., 2018,16, 5635-5642
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    Stereoselective synthesis of enantiomerically pure bowl-shaped hydroxytribenzotriquinacenes

    P. Rommelmann, B. Nachtigall, T. Guntelmann, H. Gröger and D. Kuck, Org. Biomol. Chem., 2018, 16, 5635
    DOI: 10.1039/C8OB01425F

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