6533b837fe1ef96bd12a2829

RESEARCH PRODUCT

Synthetic Approaches to Anti-Inflammatory Macrolactones of the Oxacyclododecindione Type

Markus RohrKristina RudolphJohannes TauberTill OpatzGerhard Erkel

subject

chemistry.chemical_classificationDouble bondStereochemistrymedicine.drug_classOrganic ChemistryHydroacylationTotal synthesisMetathesisRing (chemistry)Anti-inflammatoryRing-closing metathesischemistrymedicinePhysical and Theoretical ChemistryIsomerization

description

Various synthetic approaches to the oxacyclododecindione-type macrolactones, known for their potent anti-inflammatory activity, are presented. These include an attempted carbonylative ring closure, a hydroacylation route, and an approach by ring-closing metathesis and double bond isomerization, as well as a strategy including ring-closing metathesis/unsaturation. The last route allowed the preparation of a bioactive analogue of the recently described 14-deoxyoxacyclododecindione.

https://doi.org/10.1002/ejoc.201500275