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Published on: January 19, 2016
Total Synthesis of Boletopsin 11 Enabled by Directed ortho-C(sp2)-H Arylation
Meng Yao Zhang1, Russell A Barrow1
1Research School of Chemistry , Australian National University , Acton , ACT 2601 , Australia.
Abstract:
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.
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