0000000000429752
AUTHOR
Thorsten Walter
showing 8 related works from this author
Total synthesis of two potent anti-inflammatory macrolactones of the oxacyclododecindione type
2015
An esterification/Friedel-Crafts-cyclization approach permitted the first successful synthetic entry into the oxacyclododecindione subclass of the dihydroxyphenylacetic acid lactone-type natural products. This route allowed the preparation of two highly active anti-inflammatory fungal secondary metabolites 14-deoxyoxacyclododecindione and 14-deoxy-4-dechlorooxacyclododecindione as well as their 14-desmethyl analogues.
A surprising switch in absolute configuration of anti-inflammatory macrolactones.
2016
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…
Correction: Total synthesis of two potent anti-inflammatory macrolactones of the oxacyclododecindione type
2015
Correction for ‘Total synthesis of two potent anti-inflammatory macrolactones of the oxacyclododecindione type’ by Johannes Tauber et al., Org. Biomol. Chem., 2015, 13, 7813–7821.
Total synthesis and biological evaluation of seven new anti-inflammatory oxacyclododecindione-type macrolactones
2020
Through variation of our previously published total synthesis of two highly active anti-inflammatory macrolactones from the oxacyclododecindione family (J. Tauber, M. Rohr, T. Walter, G. Erkel and T. Opatz, Org. Biomol. Chem., 2015, 13, 7813-7821), seven new representatives of this compound class were prepared. Substitution of the 14-hydroxy group in oxacyclododecindione with a methyl substituent provided a readily accessible non-natural analogue which has similar pharmacological properties to the scarcely available natural product. Since the producible amount of substance is therefore no longer restricted by low fermentation yields, extensive in vivo studies become possible for the first t…
CCDC 1998325: Experimental Crystal Structure Determination
2020
Related Article: Carina Weber, Nina Vierengel, Thorsten Walter, Torsten Behrendt, Tobias Lucas, Gerhard Erkel, Till Opatz|2020|Org.Biomol.Chem.|18|5906|doi:10.1039/D0OB00958J
CCDC 1998326: Experimental Crystal Structure Determination
2020
Related Article: Carina Weber, Nina Vierengel, Thorsten Walter, Torsten Behrendt, Tobias Lucas, Gerhard Erkel, Till Opatz|2020|Org.Biomol.Chem.|18|5906|doi:10.1039/D0OB00958J
CCDC 1998324: Experimental Crystal Structure Determination
2020
Related Article: Carina Weber, Nina Vierengel, Thorsten Walter, Torsten Behrendt, Tobias Lucas, Gerhard Erkel, Till Opatz|2020|Org.Biomol.Chem.|18|5906|doi:10.1039/D0OB00958J
CCDC 1454207: Experimental Crystal Structure Determination
2016
Related Article: Johannes Tauber, Markus Rohr, Thorsten Walter, Dieter Schollmeyer, Karin Rahn-Hotze, Gerhard Erkel, Till Opatz|2016|Org.Biomol.Chem.|14|3695|doi:10.1039/C6OB00430J