Syntheses of the fungal metabolites boletopsins 7, 11, and 12 from the Papua New Guinea medicinal mushroom Boletopsis sp.
Boletopsins 7 (1), 11 (2), and 12 (3) are p-terphenyl dibenzofuran compounds, isolated from the Papua New Guinean medicinal mushroom Boletopsis sp. The first syntheses of these fungal metabolites are reported, allowing for an investigation of their antibiotic activity. The key steps include sequential Suzuki-Miyaura couplings to rapidly form the p-terphenyl backbone and an Ullmann ether synthesis on a formate ester to create the dibenzofuran moiety. Biological evaluation of the synthetic compounds and intermediates against a panel of bacterial nosocomial pathogens was performed.
Research School of Chemistry, The Australian National University , Canberra, Australian Capital Territory 0200, Australia.
Andrew M
AM
Beekman
Russell A
RA
Barrow
D000363:Agaricales / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D005658:Fungi / Q000737:chemistry*; D010219:Papua New Guinea; D013730:Terphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
D001572:Benzofurans; D013730:Terphenyl Compounds; C550056:boletopsin A