Beilstein J. Org. Chem.2017,13, 988–994, doi:10.3762/bjoc.13.98
effective synthetic protocol to access [6,6]-bicycliclactone 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]-bicycliclactone; vinyl halide; Introduction
The neuronal nicotinic acetylcholine receptors (nAChRs) have been
for aromatic erythrinanes [2] whereas only four total syntheses of lactonic erythrinanes have been published so far [13][14][15][16]. Hence, for the DHβE-based CD fragments, we faced a significantly more challenging synthesis due to the complex nature of the [6,6]-bicycliclactone moiety for which
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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...