Search

Your search keyword '"Brown, M. Kevin"' showing total 434 results
Start Over Author "Brown, M. Kevin"
434 results on '"Brown, M. Kevin"'

1. Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes

Author

Ma, Jiajia, Chen, Shuming, Bellotti, Peter, Guo, Renyu, Schäfer, Felix, Heusler, Arne, Zhang, Xiaolong, Daniliuc, Constantin, Brown, M Kevin, Houk, Kendall N, and Glorius, Frank

Subjects
Alkenes, Catalysis, Cycloaddition Reaction, Energy Transfer, Hydrocarbons, Aromatic, Molecular Structure, Quinolines, Stereoisomerism, General Science & Technology
Abstract

Dearomative cycloaddition reactions represent an ideal means of converting flat arenes into three-dimensional architectures of increasing interest in medicinal chemistry. Quinolines, isoquinolines, and quinazolines, despite containing latent diene and alkene subunits, are scarcely applied in cycloaddition reactions because of the inherent low reactivity of aromatic systems and selectivity challenges. Here, we disclose an energy transfer-mediated, highly regio- and diastereoselective intermolecular [4 + 2] dearomative cycloaddition reaction of these bicyclic azaarenes with a plethora of electronically diverse alkenes. This approach bypasses the general reactivity and selectivity issues, thereby providing various bridged polycycles that previously have been inaccessible or required elaborate synthetic efforts. Computational studies with density functional theory elucidate the mechanism and origins of the observed regio- and diastereoselectivities.

Published
2021

2. Lessons in Strain and Stability: Enantioselective Synthesis of (+)‐[5]‐Ladderanoic Acid

Author

Hancock, Erin N, Kuker, Erin L, Tantillo, Dean J, and Brown, M Kevin

Subjects
Organic Chemistry, Chemical Sciences, Biological Products, Carboxylic Acids, Cyclobutanes, Drug Stability, Stereoisomerism, copper, cycloaddition, natural products, reaction mechanisms, strained molecules, Chemical sciences
Abstract

The synthesis of structurally complex and highly strained natural products provides unique challenges and unexpected opportunities for the development of new reactions and strategies. Herein, the synthesis of (+)-[5]-ladderanoic acid is reported. En route to the target, unusual and unexpected strain release driven transformations were uncovered. This occurrence required a drastic revision of the synthetic design that ultimately led to the development of a novel stepwise cyclobutane assembly by an allylboration/Zweifel olefination sequence.

Published
2020

3. Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space.

Author

Kearney, Sara E, Zahoránszky-Kőhalmi, Gergely, Brimacombe, Kyle R, Henderson, Mark J, Lynch, Caitlin, Zhao, Tongan, Wan, Kanny K, Itkin, Zina, Dillon, Christopher, Shen, Min, Cheff, Dorian M, Lee, Tobie D, Bougie, Danielle, Cheng, Ken, Coussens, Nathan P, Dorjsuren, Dorjbal, Eastman, Richard T, Huang, Ruili, Iannotti, Michael J, Karavadhi, Surendra, Klumpp-Thomas, Carleen, Roth, Jacob S, Sakamuru, Srilatha, Sun, Wei, Titus, Steven A, Yasgar, Adam, Zhang, Ya-Qin, Zhao, Jinghua, Andrade, Rodrigo B, Brown, M Kevin, Burns, Noah Z, Cha, Jin K, Mevers, Emily E, Clardy, Jon, Clement, Jason A, Crooks, Peter A, Cuny, Gregory D, Ganor, Jake, Moreno, Jesus, Morrill, Lucas A, Picazo, Elias, Susick, Robert B, Garg, Neil K, Goess, Brian C, Grossman, Robert B, Hughes, Chambers C, Johnston, Jeffrey N, Joullie, Madeleine M, Kinghorn, A Douglas, Kingston, David GI, Krische, Michael J, Kwon, Ohyun, Maimone, Thomas J, Majumdar, Susruta, Maloney, Katherine N, Mohamed, Enas, Murphy, Brian T, Nagorny, Pavel, Olson, David E, Overman, Larry E, Brown, Lauren E, Snyder, John K, Porco, John A, Rivas, Fatima, Ross, Samir A, Sarpong, Richmond, Sharma, Indrajeet, Shaw, Jared T, Xu, Zhengren, Shen, Ben, Shi, Wei, Stephenson, Corey RJ, Verano, Alyssa L, Tan, Derek S, Tang, Yi, Taylor, Richard E, Thomson, Regan J, Vosburg, David A, Wu, Jimmy, Wuest, William M, Zakarian, Armen, Zhang, Yufeng, Ren, Tianjing, Zuo, Zhong, Inglese, James, Michael, Sam, Simeonov, Anton, Zheng, Wei, Shinn, Paul, Jadhav, Ajit, Boxer, Matthew B, Hall, Matthew D, Xia, Menghang, Guha, Rajarshi, and Rohde, Jason M

Subjects
Chemical Sciences
Abstract

Natural products and their derivatives continue to be wellsprings of nascent therapeutic potential. However, many laboratories have limited resources for biological evaluation, leaving their previously isolated or synthesized compounds largely or completely untested. To address this issue, the Canvass library of natural products was assembled, in collaboration with academic and industry researchers, for quantitative high-throughput screening (qHTS) across a diverse set of cell-based and biochemical assays. Characterization of the library in terms of physicochemical properties, structural diversity, and similarity to compounds in publicly available libraries indicates that the Canvass library contains many structural elements in common with approved drugs. The assay data generated were analyzed using a variety of quality control metrics, and the resultant assay profiles were explored using statistical methods, such as clustering and compound promiscuity analyses. Individual compounds were then sorted by structural class and activity profiles. Differential behavior based on these classifications, as well as noteworthy activities, are outlined herein. One such highlight is the activity of (-)-2(S)-cathafoline, which was found to stabilize calcium levels in the endoplasmic reticulum. The workflow described here illustrates a pilot effort to broadly survey the biological potential of natural products by utilizing the power of automation and high-throughput screening.

Published
2018

6. Synthesis of Secondary Boronates via Deaminative Cross‐Coupling of Alkyl Nitroso Carbamates and Boronic Acids.

Author

Paul, Shashwati and Brown, M. Kevin

Subjects
*FUNCTIONAL groups, *CARBAMATES, *AMINO acids, *LYSINE, *AMINES, *BORONIC acids
Abstract

A strategy for transition metal‐free cross‐coupling of alkyl nitroso‐carbamates and boronic acids is reported. The N‐nitroso carbamates are easily prepared from the corresponding amine in two simple steps. This method allows for the synthesis of a wide variety of secondary boronates, benzylic boronates and formal Csp3−Csp2 cross‐coupling products under operationally simple conditions. Functional group tolerance is also demonstrated and applied in the modification of lysine to make non‐canonical amino acids. [ABSTRACT FROM AUTHOR]

Published
2024
Full Text
View/download PDF

8. Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes

Author

Xu, Yao, Hong, Young J, Tantillo, Dean J, and Brown, M Kevin

Subjects
Alkadienes, Alkenes, Catalysis, Cycloaddition Reaction, Cyclobutanes, Molecular Structure, Chemical Sciences, Organic Chemistry
Abstract

Intramolecular chirality transfer [2 + 2] cycloaddition of enantiomerically enriched allenoates and alkenes is presented. The use of a chiral catalyst was found to be critical to achieve high levels of diastereoselectivity compared to use of an achiral catalyst. The method developed leads to highly substituted cyclobutanes that would be difficult to prepare by alternative methods.

Published
2017

17. The Highly Operational Team (HOT) toward f-Block Materials

Author

Park, Kyoung Chul, Liu, Yuan, Khashab, Niveen M., Hudson, Zachary M., Goicoechea, Jose M., Gruetzmacher, Hansjorg, Mueller, Christian, Ivanova, Mariya E., Rose, Philipp, Abdi, Fatwa F., Brendelberger, Stefan, Duran, Ines, Fantz, Ursel, Harting, Jens, Ding, Yong, Han, Xinbao, Yu, Jin, Westerlind, Ulrika, Nau, Werner M., Kalenius, Elina, Lee, Tung-Chun, Cha, Jin Wook, Park, Jin-Soo, Vojvodic, Aleksandra, Wu, Jianzhong, Meng, Xing, Liu, Chengyuan, Pan, Yang, Pakulski, Dawid, Samori, Paolo, Ciesielski, Artur, Zhao, Wengao, Wang, Kuan, Fan, Xinming, Yan, Pengfei, Yang, Yong, Xu, Lijin, Lei, Ming, Walsh, Patrick J., Prato, Maurizio, Zhang, Kai, Xia, Haiping, Giri, Ramesh, Wang, Wei, Wang, Hui, Ghorai, Prasanta, Hong, Sungwoo, Hensen, Emiel J. M., Kosinov, Nikolay, Wu, Hao, Yu, Jia, Wang, Kai, Zhang, Xiao-Hong, Gao, Ge, Liang, Gaolin, Zhang, Xu, Jiang, Nan, Fu, Yongzhu, Ohtani, Ryo, Ohba, Masaaki, Lee, Taehwan, Jung, Jaehoon, Lee, Jeong-Hwan, Lee, Min Hyung, Dou, Chuandong, Wang, Peifang, Ao, Yanhui, Luo, Junhua, Freire, Felix, Liu, Xiaohua, Feng, Xiaoming, Yu, Jie, Pu, Kanyi, Gao, De-Wei, Li, Jin-Jin, Liu, Peng, Zhou, Yin-Ning, Pan, Yun-Xiang, Li, Si, Gao, Guang-Gang, Zang, Shuang-Quan, Lee, Jeongjin, Li, Mingle, Liu, Xiaogang, Park, Jae Hyung, Kim, Jong Seung, Kumagai, Naoya, Li, Shuang, Thomas, Arne, Pachfule, Pradip, Zhao, Chuan, Pan, Yu, Hu, Anjun, Long, Jianping, Chang, Ze, Mulder, Monique P. C., Yang, Limin, Cai, Quan, Liu, Zhaowei, Nash, Michael A., Barbour, Leonard J., Walker, Alice R., Nguyen, Hien M., Zhao, Chuanqi, Liu, Zhengwei, Qu, Xiaogang, Dobbek, Holger, Cao, Chun-Shuai, Zhao, Bin, Zhang, Zhenjie, Wen, Rui, Zhang, Xue-Qiang, Yang, Dayong, Zuo, Xiaolei, Liu, Peifeng, Wu, Hongwei, Hadlington, Terrance J., Dong, Shunxi, Yan, Wenfu, Yu, Jihong, Zhang, Lu, Sun, Licheng, Hou, Jungang, Kwon, Jang Hyuk, Song, Yuefeng, Wang, Guoxiong, Liu, Yongzhuang, Yu, Haipeng, Ge, Shaozhong, Dickschat, Jeroen S., Dreuw, Andreas, Freudenberg, Jan, Casado, Juan, Bunz, Uwe H. F., Takezawa, Hiroki, Sato, Sota, Fujita, Makoto, Oguri, Hiroki, Fu, Aiping, Zhang, Yuexia, Xie, Hua, Li, Jun, Hu, Han-Shi, Jiang, Ling, Seshadri, Ram, Cheetham, Anthony K., Melchiorre, Paolo, Xia, Ying, Magauer, Thomas, Wang, Wang, Brown, M. Kevin, Waser, Jerome, Baraban, Joshua H., Umemoto, Teruo, Hammond, Gerald B., Bures, Jordi, Cornella, Josep, Kazmaier, Uli, Park, Kyoung Chul, Liu, Yuan, Khashab, Niveen M., Hudson, Zachary M., Goicoechea, Jose M., Gruetzmacher, Hansjorg, Mueller, Christian, Ivanova, Mariya E., Rose, Philipp, Abdi, Fatwa F., Brendelberger, Stefan, Duran, Ines, Fantz, Ursel, Harting, Jens, Ding, Yong, Han, Xinbao, Yu, Jin, Westerlind, Ulrika, Nau, Werner M., Kalenius, Elina, Lee, Tung-Chun, Cha, Jin Wook, Park, Jin-Soo, Vojvodic, Aleksandra, Wu, Jianzhong, Meng, Xing, Liu, Chengyuan, Pan, Yang, Pakulski, Dawid, Samori, Paolo, Ciesielski, Artur, Zhao, Wengao, Wang, Kuan, Fan, Xinming, Yan, Pengfei, Yang, Yong, Xu, Lijin, Lei, Ming, Walsh, Patrick J., Prato, Maurizio, Zhang, Kai, Xia, Haiping, Giri, Ramesh, Wang, Wei, Wang, Hui, Ghorai, Prasanta, Hong, Sungwoo, Hensen, Emiel J. M., Kosinov, Nikolay, Wu, Hao, Yu, Jia, Wang, Kai, Zhang, Xiao-Hong, Gao, Ge, Liang, Gaolin, Zhang, Xu, Jiang, Nan, Fu, Yongzhu, Ohtani, Ryo, Ohba, Masaaki, Lee, Taehwan, Jung, Jaehoon, Lee, Jeong-Hwan, Lee, Min Hyung, Dou, Chuandong, Wang, Peifang, Ao, Yanhui, Luo, Junhua, Freire, Felix, Liu, Xiaohua, Feng, Xiaoming, Yu, Jie, Pu, Kanyi, Gao, De-Wei, Li, Jin-Jin, Liu, Peng, Zhou, Yin-Ning, Pan, Yun-Xiang, Li, Si, Gao, Guang-Gang, Zang, Shuang-Quan, Lee, Jeongjin, Li, Mingle, Liu, Xiaogang, Park, Jae Hyung, Kim, Jong Seung, Kumagai, Naoya, Li, Shuang, Thomas, Arne, Pachfule, Pradip, Zhao, Chuan, Pan, Yu, Hu, Anjun, Long, Jianping, Chang, Ze, Mulder, Monique P. C., Yang, Limin, Cai, Quan, Liu, Zhaowei, Nash, Michael A., Barbour, Leonard J., Walker, Alice R., Nguyen, Hien M., Zhao, Chuanqi, Liu, Zhengwei, Qu, Xiaogang, Dobbek, Holger, Cao, Chun-Shuai, Zhao, Bin, Zhang, Zhenjie, Wen, Rui, Zhang, Xue-Qiang, Yang, Dayong, Zuo, Xiaolei, Liu, Peifeng, Wu, Hongwei, Hadlington, Terrance J., Dong, Shunxi, Yan, Wenfu, Yu, Jihong, Zhang, Lu, Sun, Licheng, Hou, Jungang, Kwon, Jang Hyuk, Song, Yuefeng, Wang, Guoxiong, Liu, Yongzhuang, Yu, Haipeng, Ge, Shaozhong, Dickschat, Jeroen S., Dreuw, Andreas, Freudenberg, Jan, Casado, Juan, Bunz, Uwe H. F., Takezawa, Hiroki, Sato, Sota, Fujita, Makoto, Oguri, Hiroki, Fu, Aiping, Zhang, Yuexia, Xie, Hua, Li, Jun, Hu, Han-Shi, Jiang, Ling, Seshadri, Ram, Cheetham, Anthony K., Melchiorre, Paolo, Xia, Ying, Magauer, Thomas, Wang, Wang, Brown, M. Kevin, Waser, Jerome, Baraban, Joshua H., Umemoto, Teruo, Hammond, Gerald B., Bures, Jordi, Cornella, Josep, and Kazmaier, Uli

Abstract

QC 20240206

Published
2023
Full Text
View/download PDF

24. Photosensitized [4+2]‐ and [2+2]‐Cycloaddition Reactions of N‐Sulfonylimines.

Author

Wang, Wang and Brown, M. Kevin

Subjects
*POLYCYCLIC compounds, *RING formation (Chemistry), *ENERGY transfer, *NATURAL products, *AZETIDINE
Abstract

The synthesis of polycyclic compounds is of high interest due to the prevalence of these motifs in drugs and natural products. Herein, we report on the stereoselective construction of 3D bicyclic scaffolds and azetidine derivatives by modulation of N‐sulfonylimines to achieve either [4+2]‐ or [2+2]‐cycloaddition reactions. The utility of the method was established by further modulation of the product. Mechanistic studies are also included, which support reaction via Dexter energy transfer. [ABSTRACT FROM AUTHOR]

Published
2023
Full Text
View/download PDF

Catalog

Books, media, physical & digital resources
See catalog results