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2. 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.

Author

Gupton JT, Yeudall S, Telang N, Hoerrner M, Huff E, Crawford E, Lounsbury K, Kimmel M, Curry W, Harrison A, Juekun W, Shimozono A, Ortolani J, Lescalleet K, Patteson J, Moore-Stoll V, Rohena CC, Mooberry SL, Obaidullah AJ, Kellogg GE, and Sikorski JA

Subjects
Animals, Antineoplastic Agents chemical synthesis, Cattle, Cell Line, Tumor, Cell Proliferation drug effects, Halogenation, Humans, Microtubules metabolism, Microtubules pathology, Molecular Docking Simulation, Neoplasms metabolism, Neoplasms pathology, Pyrroles chemical synthesis, Rats, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Cell Survival drug effects, Microtubules drug effects, Neoplasms drug therapy, Pyrroles chemistry, Pyrroles pharmacology
Abstract

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., (Copyright © 2017 Elsevier Ltd. All rights reserved.)

Published
2017
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3. 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.

Author

Gupton JT, Telang N, Wormald M, Lescalleet K, Patteson J, Curry W, Harrison A, Hoerrner M, Sobieski J, Kimmel M, Kluball E, and Perry T

Abstract

A new pyrrole building block is described, which allows for the regiospecific synthesis of 2,3,5-trisubstituted pyrroles and 2,3,4,5- tetrasubstituted pyrroles. Optimization studies are presented for the preparation of the pyrrole building block along with the evaluation of various cross-coupling conditions and cross-coupling agents. A short, formal synthesis of the natural products Polycitone A, Polycitone B and Polycitrin A from the pyrrole building block is also described.

Published
2014
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