James Panek

About

James Panek is a professor in the Department of Chemistry at Boston University. His research group emphasizes the area of synthetic organic chemistry, with a particular focus on the induction of chirality. His work involves the synthesis of new reagents and the development of new reaction methods, as well as natural product synthesis. These research activities aim to generate new methods for carrying out complex organic molecule synthesis, employing or developing innovative research techniques. Panek is affiliated with the Center for Molecular Discovery and has a background that includes a B.Sc. in Chemistry from SUNY Buffalo, an M.S. and Ph.D. in Medicinal Chemistry from Kansas University, and a postdoctoral fellowship at Yale University. His educational and research background supports his contributions to advancing the understanding and methodology of organic synthesis.

Research topics

• Combinatorial chemistry
• Chemistry
• Organic chemistry
• Computational chemistry
• Stereochemistry

Selected publications

• Multicomponent Condensation Reactions via <i>ortho</i>-Quinone Methides

  Organic Letters · 2017-03-30 · 59 citations

  article

  Iron(III) salts promote the condensation of aldehydes or acetals with electron-rich phenols to generate ortho-quinone methides that undergo Diels-Alder condensations with alkenes. The reaction sequence occurs in a single vessel to afford benzopyrans in up to 95% yield. The reaction was discovered while investigating a two-component strategy using 2-(hydroxy(phenyl)methyl)phenols to access the desired ortho-quinone methide in a Diels-Alder condensation. The two-component condensation also afforde…

  PublisherDOI

• Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols

  Organic Letters · 2015-11-18 · 43 citations

  article

  Chiral diols and biphenols catalyze the multicomponent condensation reaction of phenols, aldehydes, and alkenyl or aryl boronates. The condensation products are formed in good yields and enantioselectivities. The reaction proceeds via an initial Friedel-Crafts alkylation of the aldehyde and phenol to yield an ortho-quinone methide that undergoes an enantioselective boronate addition. A cyclization pathway was discovered while exploring the scope of the reaction that provides access to chiral 2,4…

  PublisherDOI

• Total Synthesis of (+)-Isatisine A: Application of a Silicon-Directed Mukaiyama-Type [3 + 2]-Annulation

  The Journal of Organic Chemistry · 2015-03-04 · 35 citations

  articleSenior author

  Complete details of an asymmetric synthesis of (+)-isatisine A (1) are described. The synthesis highlights the use of a highly diastereoselective Mukaiyama-type [3 + 2]-annulation of allylsilane 5 with the unsaturated aldehyde 9a to assemble the functionalized tetrahydrofuran core of isatisine A. A convergent route to the framework of the natural product was established that employed a substrate-controlled indole coupling that was followed by a late-stage intramolecular copper(I)-mediated amidat…

  PublisherDOI

• Rhodium(II)-Catalyzed Alkyne Amination of Homopropargylic Sulfamate Esters: Stereoselective Synthesis of Functionalized Norcaradienes by Arene Cyclopropanation

  Organic Letters · 2013-12-16 · 35 citations

  articleSenior author

  A rhodium(II) catalyzed nitrene-alkyne cycloaddition of stereochemically well-defined homopropargylic ethers is followed by arene cyclopropanation to afford unique tetracyclic norcaradiene products bearing a cyclic sulfamate. Products from the arene cyclopropanation (Buchner reaction) can be converted to fused cycloheptatrienes via a ring enlarging electrocyclization after nucleophilic ring opening of the cyclic sulfamate ester.

  PublisherDOI

• Convergent Synthesis of Novel Muramyl Dipeptide Analogues: Inhibition of <i>Porphyromonas gingivalis</i>-Induced Pro-inflammatory Effects by High Doses of Muramyl Dipeptide

  Journal of Medicinal Chemistry · 2016-06-29 · 22 citations

  article

  Porphyromonas gingivalis (P.g.)-induced TNF-α can be affected by muramyl dipeptide (MDP) in a biphasic concentration-dependent manner. We found that in P.g.-exposed macrophages, treatment with 10 μg/mL of MDP (MDP-low) up-regulated TNF-α by 29%, while 100 μg/mL or higher (MDP-high) significantly decreased it (16% to 38%). MDP-high was found to affect the ubiquitin-editing enzyme A20 and activator protein 1 (AP1). An AP1 binding site was found in the promoter region of A20. A20 promoter activity…

  PublisherDOI

Recent grants

• NIH Grant R01GM055740

  NIH · $1.8M · 2008

• NIH Grant R01CA056304

  NIH · $3.1M · 2008

Frequent coauthors

• John A. Porco

  46 shared

• Aaron B. Beeler

  35 shared

• Jason T. Lowe

  Foghorn Therapeutics (United States)

  27 shared

• Dale L. Boger

  Scripps Research Institute

  27 shared

• Qibin Su

  AstraZeneca (United States)

  26 shared

• C. E. Masse

  26 shared

• Les A. Dakin

  AstraZeneca (United States)

  22 shared

• Bryan L. Roth

  University of North Carolina at Chapel Hill

  19 shared

Education

• MS, PhD, Medicinsl Chemistyr

  Kansas University

Similar researchers at Boston University

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• Tom Tulliush-57
• Karen Allenh-56