A surprising switch in absolute configuration of anti-inflammatory macrolactones-Reference-Cited by-同舟云学术

A surprising switch in absolute configuration of anti-inflammatory macrolactones

Published:2016 Issue:15 Volume:14 Page:3695-3698
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Tauber Johannes¹²³⁴,Rohr Markus⁵⁶⁷⁴,Walter Thorsten⁵⁶⁷⁴,Schollmeyer Dieter¹²³⁴,Rahn-Hotze Karin⁸⁹¹⁰⁴,Erkel Gerhard⁵⁶⁷⁴,Opatz Till¹²³⁴

Affiliation:

1. Institute of Organic Chemistry

2. Johannes Gutenberg-University

3. 55128 Mainz

4. Germany

5. Department of Molecular Biotechnology & Systems Biology

6. University of Kaiserslautern

7. 67663 Kaiserslautern

8. R&D LGCR/Chemistry FF

9. Sanofi GmbH

10. D-65926 Frankfurt am Main

Abstract

The absolute configuration of the strongly anti-inflammatory 14-deoxyoxacyclododecindione was determined as (14S,15R) which is opposite to the configuration of the structurally related but less bioactive (S)-curvularin.

Funder

Carl-Zeiss-Stiftung

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2016/OB/C6OB00430J

Reference23 articles.

1. 828. Curvularin. Part I. Isolation and partial characterisation of a metabolic product from a new species of Curvularia

2. 4-Dechloro-14-deoxy-oxacyclododecindione and 14-deoxy-oxacylododecindione, two inhibitors of inducible connective tissue growth factor expression from the imperfect fungus Exserohilum rostratum

3. Oxacyclododecindione, a Novel Inhibitor of IL-4 Signaling from Exserohilum rostratum

4. 2-(Trimethylsilyl)�thylester als Carboxylschutzgruppe; Anwendung bei der Synthese des (?)-(S)-Curvularins

5. A Chemoenzymatic Synthesis of The Macrocyclic Lactone (S)-Curvularin

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