Total Synthesis of Benzofuran-Based Aspergillusene B via Halogenative Aromatization of Enones.

A novel "non-aromatic pool" synthetic strategy for the synthesis of benzofuran-based natural products via oxidative haloaromatization of enones is reported. This approach is successfully applied in the first total synthesis of the natural product aspergillusene B. In comparison with a separately executed "aromatic pool" synthesis, the "non-aromatic pool" protocol demonstrates equivalent efficiency but offers a much higher degree of modularity.

Short Enantioselective Formal Synthesis of (-)-Platencin.

A short enantioselective formal synthesis of the antibiotic natural product platencin is reported. Key steps in the synthesis include enantioselective decarboxylation alkylation, aldehyde/olefin radical cyclization, and regioselective aldol cyclization.

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands.

Cu- and Pd-catalyzed arylation of aminocholanes has been described for the first time. While this Cu-catalyzed protocol provides high yields in reactions of aminocholanes with iodoarenes, Pd catalysis was found to be preferable for the reactions of aminocholanes with dichloroanthraquinones. UV-vis titration of bis(cholanylamino)anthraquinones with a series of cations demonstrated their high binding affinity to Cu2+, Al3+, and Cr3+.

Total Synthesis of Grifolin, Grifolic Acid, LL-Z1272α, LL-Z1272ß, and Ilicicolinic Acid A.

A novel synthetic approach for the synthesis of bioactive phenolic natural products is reported. This strategy highlights the power of halogenative aromatization reactions recently developed in our group for preparing densely functionalized arenes in a controlled fashion. Five natural products related by an aromatic core and a farnesyl side chain are synthesized. In contrast to prior methods, this synthesis features high efficiency and generality that permits preparation of targets in gram-scale quantities.