We have successfully accomplished a catalytic asymmetric total synthesis of entecavir, a first-line antihepatitis B virus medication. The pivotal aspect of our strategy lies in the utilization of a Pd-catalyzed enyne borylative cyclization reaction, enabling the construction of a highly substituted cyclopentene scaffold with exceptional stereoselectivity. Additionally, we efficiently accessed the crucial 1,3-diol enyne system early in our synthetic route through a diarylprolinol organocatalyzed enantioselective cross-aldol reaction and Re-catalyzed allylic alcohol relocation.
View Article and Find Full Text PDFDevelopment of efficient and stereoselective synthesis of prostaglandins (PGs) is of utmost importance, owing to their valuable medicinal applications and unique chemical structures. We report here a unified synthesis of PGs cloprostenol, bimatoprost, PGF, fluprostenol, and travoprost from the readily available dichloro-containing bicyclic ketone guided by biocatalytic retrosynthesis, in 11-12 steps with 3.8-8.
View Article and Find Full Text PDFDiazo compounds play an important role as a coupling partner in the synthesis of unique π-conjugated 7-azaindole derivatives via rhodium(iii)-catalyzed double C-H activation/cyclization.
View Article and Find Full Text PDFA convenient rhodium(III)-catalyzed cascade reaction of 7-azaindoles and alkynes through multiple C-H bond activation for the synthesis of unique [5]azahelicenes has been developed. The optical property of these screw-shaped helicene derivatives could be further utilized in electronic devices to recognize mercury ions.
View Article and Find Full Text PDFAn efficient rhodium-catalyzed dehydrogenative Heck-type reaction between N-aryl-substituted 7-azaindoles and various alkenes through a H -releasing process without the need of any oxidizing agent was developed. The novel methodology broadens the scope of metal-catalyzed hydrogen-releasing reactions to include rhodium catalysis.
View Article and Find Full Text PDFA novel one-pot synthesis of π-conjugated polycyclic compounds, which could undergo further facile transformation to form complex polycyclic heteroarene compounds, has been realized between 7-azaindoles and α,β-unsaturated ketones. This distinctive cascade process proceeds via a rhodium(iii)-catalyzed alkylation/copper-catalyzed radical annulation-aromatization pathway.
View Article and Find Full Text PDFRhodium(iii)-catalyzed N-directed ortho C-H activation and subsequent roll-over C-H activation represents an important strategy to synthesize fused polycyclic compounds. Herein, the novel methodology broadens the scope of the coupling partner to alkenes, which working smoothly with 7-azaindoles has been proven to be an efficient and atom-economical strategy to access complex π-conjugated 7-azaindole derivatives.
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