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Issue 15, 2016
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A surprising switch in absolute configuration of anti-inflammatory macrolactones

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Abstract

Oxacyclododecindione-type macrolactones exhibit highly potent anti-inflammatory activities even at nanomolar concentration. After the determination of the relative configuration of the stereocenters at C14 and C15 by total synthesis of 4-dechloro-14-deoxyoxacyclododecindione and 14-deoxyoxacyclododecindione, the absolute configuration has now been assigned by X-ray crystallography. Surprisingly, the absolute configuration is (14S,15R) which differs for C15 from that of the well-known derivatives of (S)-curvularin. The biological activities of both enantiomers of 14-deoxyoxacyclododecindione, obtained by racemic synthesis and optical resolution, were investigated and the ring conformation of the natural product was compared to that of (S)-curvularin and (R)-dehydrocurvularin.

Graphical abstract: A surprising switch in absolute configuration of anti-inflammatory macrolactones

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Publication details

The article was received on 24 Feb 2016, accepted on 17 Mar 2016 and first published on 22 Mar 2016


Article type: Communication
DOI: 10.1039/C6OB00430J
Org. Biomol. Chem., 2016,14, 3695-3698
  • Open access: Creative Commons BY-NC license
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    A surprising switch in absolute configuration of anti-inflammatory macrolactones

    J. Tauber, M. Rohr, T. Walter, D. Schollmeyer, K. Rahn-Hotze, G. Erkel and T. Opatz, Org. Biomol. Chem., 2016, 14, 3695
    DOI: 10.1039/C6OB00430J

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