A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE.

Beilstein J Org Chem

Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark.

Published: May 2017

We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki-Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the alkaloid DHβE. Preliminary pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480346PMC
http://dx.doi.org/10.3762/bjoc.13.98DOI Listing

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