1541073-10-2Relevant academic research and scientific papers
Total Synthesis of Boletopsin 11 Enabled by Directed ortho-C(sp2)-H Arylation
Zhang, Meng Yao,Barrow, Russell A.
, p. 6776 - 6782 (2018)
A nine-step synthesis of boletopsin 11 (1), a bioactive fungal natural product, is disclosed. Key features include a one-pot [O]-oxa-Michael cascade to establish the polyoxygenated dibenzofuran core followed by a Pd-catalyzed directed ortho-C(sp2)-H arylation to complete the fully functionalized carbon skeleton. Exploration of the latter transformation led to the discovery of an unexpected tandem ortho-C(sp2)-H arylation event, and the scope of the directed ortho-C(sp2)-H reaction was further investigated with coupling partners varying in stereoelectronic properties.
Syntheses of the fungal metabolites Boletopsins 7, 11, and 12 from the Papua New Guinea medicinal mushroom Boletopsis sp.
Beekman, Andrew M.,Barrow, Russell A.
, p. 1017 - 1024 (2014/03/21)
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.
