Synthesis of pterocellin A.
The first total synthesis of pterocellin A (1) was achieved in 10 linear steps from commercially available kojic acid (6) and 2-bromo-3-pyridinol (11) in a convergent sequence. The key constructive steps are a directed lithiation to couple two pyridines and an intramolecular nucleophilic aromatic substitution to form 1. [structure: see text]
O'Malley
Meaghan M
MM
E. F. Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Damkaci
Fehmi
F
Kelly
T Ross
TR
D000470:Alkaloids / Q000138:chemical synthesis*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry
D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D011753:Pyrones; C479813:pterocellin A; C011890:kojic acid