Jump to main content
Jump to site search

Issue 15, 2016
Previous Article Next Article

A surprising switch in absolute configuration of anti-inflammatory macrolactones

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
24 Feb 2016
Accepted
17 Mar 2016
First published
22 Mar 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 3695-3698
Article type
Communication

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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements