John Gupton

Find an error

Name:

Organization: University of Richmond

Department: Department of Chemistry

Title:

TOPICS

Organic Chemistry

suzuki-miyaura Coupling

Chemicals
References

Ortho group activation of a bromopyrrole ester in Suzuki-Miyaura cross-coupling reactions: Application to the synthesis of new microtubule depolymerizing agents with potent cytotoxic activities

Co-reporter:John T. Gupton, Scott Yeudall, Nakul Telang, Megan Hoerrner, Ellis Huff, Evan Crawford, Katie Lounsbury, Michael Kimmel, William Curry, Andrew Harrison, Wen Juekun, Alex Shimozono, Joe Ortolani, Kristin Lescalleet, Jon Patteson, Veronica Moore-Stoll, Cristina C. Rohena, Susan L. Mooberry, Ahmad J. Obaidullah, Glen E. Kellogg, James A. Sikorski, et al.

Bioorganic & Medicinal Chemistry 2017 Volume 25, Issue 12(Issue 12) pp:

Publication Date(Web):15 June 2017

DOI:10.1016/j.bmc.2017.04.012

New microtubule depolymerizing agents with potent cytotoxic activities have been prepared with a 5-cyano or 5-oximino group attached to a pyrrole core. The utilization of ortho activation of a bromopyrrole ester to facilitate successful Suzuki-Miyaura cross-coupling reactions was a key aspect of the synthetic methodology. This strategy allows for control of regiochemistry with the attachment of four completely different groups at the 2, 3, 4 and 5 positions of the pyrrole scaffold. Biological evaluations and molecular modeling studies are reported for these examples.Download high-res image (99KB)Download full-size image

The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether

Co-reporter:John T. Gupton, Nakul Telang, Jon Patteson, Kristin Lescalleet, Scott Yeudall, John Sobieski, Andrew Harrison, Will Curry

Tetrahedron 2014 70(52) pp: 9759-9767

Publication Date(Web):

DOI:10.1016/j.tet.2014.11.035

Formyl group activation of a bromopyrrole ester in Suzuki cross-coupling reactions: application to a formal synthesis of Polycitone A and B and Polycitrin A

Co-reporter:John T. Gupton, Nakul Telang, Michael Wormald, Kristin Lescalleet, Jon Patteson, Will Curry, Andrew Harrison, Megan Hoerrner, John Sobieski, Michael Kimmel, Emily Kluball, Thomas Perry

Tetrahedron 2014 70(17) pp: 2738-2745

Publication Date(Web):

DOI:10.1016/j.tet.2014.02.091

Preparation of indole containing building blocks for the regiospecific construction of indole appended pyrazoles and pyrroles

Co-reporter:John T. Gupton, Nakul Telang, Dominic F. Gazzo, Peter J. Barelli, Kristin E. Lescalleet, Jonathan W. Fagan, Brandon J. Mills, Kara L. Finzel, Rene P.F. Kanters, Kyle R. Crocker, Sean T. Dudek, Corinne M. Lariviere, Stanton Q. Smith, Kartik M. Keertikar

Tetrahedron 2013 69(29) pp: 5829-5840

Publication Date(Web):

DOI:10.1016/j.tet.2013.05.045

Further studies on vinamidinium salt amine exchange reactions, borohydride reductions, and subsequent transformations

Co-reporter:John T. Gupton, Nakul Telang, Xin Jia, Benjamin C. Giglio, James E. Eaton, Peter J. Barelli, Mona Hovaizi, Kayleigh E. Hall, R. Scott Welden, Matthew J. Keough, Eric F. Worrall, Kara L. Finzel, Emily J. Kluball, Rene P.F. Kanters, Timothy M. Smith, Stanton Q. Smith, Shane R. Nunes, Mathew T. Wright, Jennifer M. Birnstihl

Tetrahedron 2010 66(44) pp: 8485-8493

Publication Date(Web):

DOI:10.1016/j.tet.2010.08.075

The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones

Co-reporter:John T. Gupton, Nakul Telang, Edith J. Banner, Emily J. Kluball, Kayleigh E. Hall, Kara L. Finzel, Xin Jia, Spencer R. Bates, R. Scott Welden, Benjamin C. Giglio, James E. Eaton, Peter J. Barelli, Lauren T. Firich, John A. Stafford, Matthew B. Coppock, Eric F. Worrall, Rene P.F. Kanters, Kerry Keertikar, Rebecca Osterman

Tetrahedron 2010 66(47) pp: 9113-9122

Publication Date(Web):

DOI:10.1016/j.tet.2010.09.080

The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine alkaloids lamellarin G trimethyl ether and ningalin B

Co-reporter:John T. Gupton, Benjamin C. Giglio, James E. Eaton, Elizabeth A. Rieck, Kristin L. Smith, Matthew J. Keough, Peter J. Barelli, Lauren T. Firich, Jonathan E. Hempel, Timothy M. Smith, Rene P.F. Kanters

Tetrahedron 2009 65(22) pp: 4283-4292

Publication Date(Web):

DOI:10.1016/j.tet.2009.03.085