Silver-catalyzed one-pot synthesis of arylnaphthalene lactone natural products.
Naturally occurring arylnaphthalene lactone lignans have demonstrated a variety of valuable medicinal chemistry properties and have therefore been of continued interest to drug discovery research. Our group has demonstrated a silver-catalyzed one-pot synthesis of the arylnaphthalene lactone core using carbon dioxide, phenylpropargyl chloride, and phenylacetylene. This new approach has been employed in the synthesis of six arylnaphthalene lactone natural products: retrochinensin (1), justicidin B (2), retrojusticidin B (3), chinensin (4), justicidin E (5), and taiwanin C (6). Additionally, an arylnaphthalene lactone regioisomer was isolated (9), which we refer to as isoretrojusticidin B.
Foley
Patrick
P
Center for Green Chemistry and Green Engineering at Yale University, 225 Prospect Street, New Haven, Connecticut 06511, USA.
Eghbali
Nicolas
N
Anastas
Paul T
PT
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
D001688:Biological Products; D007783:Lactones; D017705:Lignans; D009281:Naphthalenes; C496008:retrojusticidin B; C467766:taiwanin C; D012834:Silver