Beilstein J. Org. Chem.2017,13, 988–994, doi:10.3762/bjoc.13.98
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 Erythrina alkaloid DHβE. Preliminary
pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings.
Keywords: DhβE; Mizoroki–Heck cross-coupling reaction; 6π-electrocyclization; [6,6]-bicyclic lactone; vinyl halide; Introduction
The neuronal nicotinic acetylcholine receptors (nAChRs) have been
extensively investigated as potential drug targets for a diverse array of central nervous system (CNS) related medical conditions such as Alzheimer’s and Parkinson’s disease, depression, ADHD, pain relief, nicotine addiction and drug abuse [1]. Dihydro-β-erythroidine (DHβE) is a member of the family of
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Graphical Abstract
Figure 1:
DHβE and related structures. The Ki values of the compounds at the rat α4β2 nAChR subtype determine...