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Issue 29, 2015
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Paleo-soraphens: chemical total syntheses and biological studies

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Abstract

The soraphens are natural products that exhibit a molecular structure different from what would have been expected by following its polyketidal assembly line. The most significant differences are the presence of a hemiketal instead of a trisubstituted double bond and a double bond at C9 and C10 where a saturated carbon chain was expected. We were interested in the biological activity of the soraphens with architectures as described by the polyketide synthase since we hypothesized that these modifications reflect the evolutionary optimization of the soraphens. Herein we describe four additional derivatives of the so-called paleo-soraphens and their biological profiling to provide a picture of the hypothetical evolutionary optimization of this family of natural products. The syntheses required a unified and convergent strategy and their biological profiling was performed with the aid of impedance measurements. The results of these biological experiments are consistent with the proposed evolutionary optimization of the soraphens.

Graphical abstract: Paleo-soraphens: chemical total syntheses and biological studies

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Publication details

The article was received on 04 May 2015, accepted on 19 Jun 2015 and first published on 19 Jun 2015


Article type: Paper
DOI: 10.1039/C5OB01249J
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Org. Biomol. Chem., 2015,13, 8029-8036

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    Paleo-soraphens: chemical total syntheses and biological studies

    H. Lu, B. Hinkelmann, T. Tautz, J. Li, F. Sasse, R. Franke and M. Kalesse, Org. Biomol. Chem., 2015, 13, 8029
    DOI: 10.1039/C5OB01249J

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