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Your search keyword '"Schnaderbeck, Matthew J."' showing total 11 results
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11 results on '"Schnaderbeck, Matthew J."'

1. REM-422, a Potent, Selective, Oral Small Molecule mRNA Degrader of the MYB Oncogene, Demonstrates Anti-Tumor Activity in Mouse Xenograft Models of AML

Author

Prajapati, Sudeep, Cameron, Michael, Dunyak, Bryan M., Shan, Mengge, Siu, Y. Amy, Levin-Furtney, Samantha, Powe, Joshua, Burchfiel, Eileen T.M., Cabral, Sarah E., Harney, Alycen M., Keenan, Regina K., Larpenteur, Kevin M., Maag, Jesper L.V., Snyder, Andrew R., Nguyen, Dan T., Blaustein, Cecile, Buonamici, Silvia, Reynolds, Dominic, Schnaderbeck, Matthew J., Seiler, Michael, Vaillancourt, Frédéric H., Smith, Peter, Kaprielian, Zaven, and Kung, Charles

Published
2023
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6. Process Development of Halaven®: Synthesis of the C1–C13 Fragment from D-(–)-Gulono-1,4-lactone.

Author

Chase, Charles E., Fang, Francis G., Lewis, Bryan M., Wilkie, Gordon D., Schnaderbeck, Matthew J., and Zhu, Xiaojie

Subjects
ORGANIC synthesis, CARBOHYDRATES, CHIRAL drugs, GLYCOSYLATION, STEREOSELECTIVE reactions
Abstract

A 12-step kilogram-scale synthesis of the C1-C13 fragment, common to halichondrin B and the totally synthetic analogue Halaven® (E7389, INN eribulin mesylate), is described. The synthesis features four crystalline intermediates which facilitates throughput, and enhances quality control of all stereogenic centers in the title compound. [ABSTRACT FROM AUTHOR]

Published
2013
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7. Commercial Manufacture of Halaven®: Chemoselective Transformations En Route to Structurally Complex Macrocyclic Ketones.

Author

Austad, Brian C., Calkins, Trevor L., Chase, Charles E., Fang, Francis G., Horstmann, Thomas E., Hu, Yongbo, Lewis, Bryan M., Niu, Xiang, Noland, Thomas A., Orr, John D., Schnaderbeck, Matthew J., Zhang, Huiming, Asakawa, Naoki, Asai, Naoki, Chiba, Hiroyuki, Hasebe, Takashi, Hoshino, Yorihisa, Ishizuka, Hiroyuki, Kajima, Takashi, and Kayano, Akio

Subjects
DRUG synthesis, CHEMOSELECTIVITY, METHANESULFONATES, KETONE synthesis, STEREOSELECTIVE reactions, COUPLING reactions (Chemistry), CARBANIONS, SULFONES
Abstract

The evolution of the synthesis of Halaven® (E7389, INN eribulin mesylate) from a medicinal chemistry process to the execution of the final process on pilot scale is described. The completion of the synthesis of Halaven® from C1-C13 ester and C14-C35 sulfone alcohol involves a series of chemo-, regio-, and stereoselective transformations. Furthermore, a high-dilution macrocyclization presented a number of challenges for industrial-scale manufacture (throughput, processing time, and side reactions). This paper describes studies at Eisai leading to an understanding, optimization, and control of the chemistry that realized the reproducible commercial production of Halaven®. [ABSTRACT FROM AUTHOR]

Published
2013
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8. Process Development of Halaven®: Synthesis of the C14–C35 Fragment via Iterative Nozaki-Hiyama-Kishi Reaction-Williamson Ether Cyclization.

Author

Austad, Brian C., Benayoud, Farid, Calkins, Trevor L., Campagna, Silvio, Chase, Charles E., Hyeong-wook Choi, Christ, William, Costanzo, Robert, Cutter, James, Endo, Atsushi, Fang, Francis G., Hu, Yongbo, Lewis, Bryan M., Lewis, Michael D., McKenna, Shawn, Noland, Thomas A., Orr, John D., Pesant, Marc, Schnaderbeck, Matthew J., and Wilkie, Gordon D.

Subjects
ANTINEOPLASTIC agent synthesis, ASYMMETRIC synthesis, NICKEL, CHROMIUM, RING formation (Chemistry), STEREOSELECTIVE reactions
Abstract

Multikilogram manufacturing process of the Halaven® C14-C35 fragment is described. The synthesis features convergent assembly of subunits by iterative asymmetric Ni/Cr-mediated coupling executed in fixed equipment. [ABSTRACT FROM AUTHOR]

Published
2013
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9. Erratum: Commercial Manufacture of Halaven®: Chemoselective Transformations En Route to Structurally Complex Macrocyclic Ketones.

Author

Austad, Brian C., Calkins, Trevor L., Chase, Charles E., Fang, Francis G., Horstmann, Thomas E., Hu, Yongbo, Lewis, Bryan M., Xiang Niu, Noland, Thomas A., Orr, John D., Schnaderbeck, Matthew J., Zhang, Huiming, Asakawa, Naoki, Asai, Naoki, Chiba, Hiroyuki, Hasebe, Takashi, Hoshino, Yorihisa, Ishizuka, Hiroyuki, Kajima, Takashi, and Kayano, Akio

Subjects
SPELLING errors
Abstract

A correction to the article "Commercial Manufacture of Halaven®: Chemoselective Transformations En Route to Structurally Complex Macrocyclic Ketones," by Brian C. Austad and colleagues that was published in the 2013 issue is presented.

Published
2013
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10. Erratum: Process Development of Halaven®: Synthesis of the C14–C35 Fragment via Iterative Nozaki-Hiyama-Kishi Reaction-Williamson Ether Cyclization.

Author

Austad, Brian C., Benayoud, Farid, Calkins, Trevor L., Campagna, Silvio, Chase, Charles E., Hyeong-wook Choi, Christ, William, Costanzo, Robert, Cutter, James, Endo, Atsushi, Fang, Francis G., Hu, Yongbo, Lewis, Bryan M., Lewis, Michael D., McKenna, Shawn, Noland, Thomas A., Orr, John D., Pesant, Marc, Schnaderbeck, Matthew J., and Wilkie, Gordon D.

Subjects
SPELLING errors
Abstract

A correction to the article "Process Development of Halaven®: Synthesis of the C14–C35 Fragment via Iterative Nozaki-Hiyama-Kishi Reaction-Williamson Ether Cyclization," by Brian C. Austad and colleagues that was published in the 2013 issue is presented.

Published
2013
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11. Erratum: Process Development of Halaven®: Synthesis of the C1–C13 Fragment from D-(–)-Gulono-1,4-lactone.

Author

Chase, Charles E., Fang, Francis G., Lewis, Bryan M., Wilkie, Gordon D., Schnaderbeck, Matthew J., and Xiaojie Zhu

Subjects
SPELLING errors
Abstract

A correction to the article "Process Development of Halaven®: Synthesis of the C1-C13 Fragment from D-(&#8211)-Gulono-1,4-lactone," by Charles E. Chase and colleagues that was published in the 2013 issue is presented.

Published
2013
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