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Design, synthesis, and evaluation of cystargolide-based β-lactones as potent proteasome inhibitors.
The novel drug lead 5k is a more potent proteasome inhibitor than carfilzomib with mid-to-low nanomolar IC50 measurements and it is cytotoxic against multiple cancer cell lines at levels approaching those of carfilZomib.
Ni-Catalyzed Regioselective 1,2-Dialkylation of Alkenes Enabled by the Formation of Two C(sp3)-C(sp3) Bonds.
This alkene dialkylation is effective in combining secondary benzyl halides and secondary alkylzinc reagents with internal alkenes, which furnishes products with three contiguous all-carbon secondary stereocenters.
Total synthesis and absolute stereochemistry of the proteasome inhibitors cystargolides A and B.
Evaluation of synthetic cystargolides and derivatives showed that the natural (2S,3R) stereochemistry is essential for activity, and benzyl esters (-)-10 and (-)-15 were found to be about 100 times more potent, and to selectively kill MCF-7 cancerous cells.
Walking metals: catalytic difunctionalization of alkenes at nonclassical sites
Judged by the number of reports emerging recently, it is now strikingly evident that the field of alkene difunctionalization by metal migration has begun to gain momentum, which holds a great future prospect to develop into a synthetic method of enormous potential.
Ni-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination.
A nickel-catalyzed reaction was disclosed, which enabled us to difunctionalize unactivated γ,δ-alkenes in ketones with alkenyl triflates and arylboronic esters, and control experiments indicate that carbonyl coordination is required for the reaction to proceed.
A total synthesis of (-)-Hortonone C.
Comparison of optical rotation data confirmed that the absolute configuration of natural hortonone C is (6S,7S,10S), and its absolute stereochemistry confirmed.
Design, synthesis, and evaluation of cystargolide-based beta-lactones as potent proteasome inhibitors.
The peptidic β-lactone proteasome inhibitors (PIs) cystargolides A and B were used to conduct structure-activity relationship (SAR) studies in order to assess their anticancer potential. A total of
Ni-Catalyzed Arylbenzylation of Alkenylarenes. Kinetic Studies Reveal Autocatalysis by ZnX2.
Kinetic studies reveal that the reaction proceeds with a rate-limiting single electron transfer process and is autocatalyzed by in situ -generated ZnX 2 .The reaction rate is amplified by three-fold through autoc atalysis upon addition of ZnZ 2 .
An Expedient Route to 9-arylmethylanthracene Derivatives via Tandem Ni-catalyzed Alkene Dicarbofunctionalization and Acid-promoted Cyclization-aromatization.
A nickel-catalyzed one pot synthesis of 9-arylmethylanthracene motifs, which find applications in medicinal and material chemistry, is reported, which can be synthesized in good yields.
Ni-Catalyzed Arylbenzylation of Alkenylarenes. Kinetic Studies Reveal Autocatalysis by ZnX2 and 3-Fold Catalytic Rate Increase
We report a Ni-catalyzed regioselective arylbenzylation of alkenylarenes with benzyl halides and arylzinc reagents. The reaction furnishes differently substituted 1,1,3-triarylpropyl structures that