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17 results on '"Jason D. Burch"'

1. Total Synthesis of Aflastatin A

Author

David A. Evans, Jason J. Beiger, Jason D. Burch, Peter H. Fuller, Frank Glorius, Egmont Kattnig, David A. Thaisrivongs, William C. Trenkle, Joseph M. Young, and Jing Zhang

Subjects
Aldehydes, Colloid and Surface Chemistry, Molecular Structure, Stereoisomerism, General Chemistry, Biochemistry, Catalysis, Pyrrolidinones, Boron
Abstract

The total syntheses of aflastatin A and its C3-C48 degradation fragment (

Published
2022

2. Could AlphaFold revolutionize chemical therapeutics?

Author

Alexander B, Tong, Jason D, Burch, Daniel, McKay, Carlos, Bustamante, Michael A, Crackower, and Hao, Wu

Subjects
Protein Conformation, Drug Design, Knowledge Bases, Computational Biology, Proteins, Databases, Protein, Algorithms
Published
2021

3. Novel pyridone EP

Author

Stéphane, Dorich, Jennifer H, Cox, Jason D, Burch, Félix, Chagnon, Bin, Chen, Serge, Léger, Miguel, St-Onge, and Lee D, Fader

Subjects
Structure-Activity Relationship, Propanols, Pyridones, Humans, Protein Isoforms, Receptors, Prostaglandin E, EP4 Subtype
Abstract

Novel prostaglandin E2 receptor 4 (EP

Published
2020

4. Comprehensive Accounts of Pharmaceutical Research and Development: From Discovery to Late-Stage Process Development Volume 1

Author

Ahmed F. Abdel-Magid, Jaan A. Pesti, Rajappa Vaidyanathan, Debra J. Wallace, Ian Mangion, Paul Coleman, Seb Caille, John G. Allen, Xianglin Shi, William F. Kiesman, Donald G. Walker, Hidenori Takahashi, Alessandra Bartolozzi, Thomas Simpson, Keith Fandrick, Jason Mulder, Jean-Nicolas Desrosiers, Nitin Patel, Xingzhong Zeng, Daniel Fandrick, Carl A. Busacca, Jinhua J. Song, Chris H. Senanayake, Timothy P. Heffron, Andrew McClory, Andreas Stumpf, Jason D. Burch, Benjamin D. Sherry, Donald R. Gauthier, Louis-Charles Campeau, Jessica E. Reed, Jeff B. Smaill, Shu Yu, Olivier Dirat, Jed L. Hubbs, Nathan O. Fuller, Wesley F. Austin, Ruichao Shen, Brian S. Bronk, Gerald J. Tanoury, Stephen Eastham, Cristian L. Harrison, Benjamin J. Littler, Piero L. Ruggiero, Zhifeng Ye, Anne-Laure Grillo, Ahmed F. Abdel-Magid, Jaan A. Pesti, Rajappa Vaidyanathan, Debra J. Wallace, Ian Mangion, Paul Coleman, Seb Caille, John G. Allen, Xianglin Shi, William F. Kiesman, Donald G. Walker, Hidenori Takahashi, Alessandra Bartolozzi, Thomas Simpson, Keith Fandrick, Jason Mulder, Jean-Nicolas Desrosiers, Nitin Patel, Xingzhong Zeng, Daniel Fandrick, Carl A. Busacca, Jinhua J. Song, Chris H. Senanayake, Timothy P. Heffron, Andrew McClory, Andreas Stumpf, Jason D. Burch, Benjamin D. Sherry, Donald R. Gauthier, Louis-Charles Campeau, Jessica E. Reed, Jeff B. Smaill, Shu Yu, Olivier Dirat, Jed L. Hubbs, Nathan O. Fuller, Wesley F. Austin, Ruichao Shen, Brian S. Bronk, Gerald J. Tanoury, Stephen Eastham, Cristian L. Harrison, Benjamin J. Littler, Piero L. Ruggiero, Zhifeng Ye, and Anne-Laure Grillo

Subjects
Chemistry, Pharmaceutical--methods, Drug Discovery, Technology, Pharmaceutical, Pharmaceutical Preparations--chemistry
Published
2016

5. Synthesis and Confirmation of the Absolute Stereochemistry of the (−)-Aflastatin A C9−C27 Degradation Polyol

Author

William C. Trenkle, Jason D. Burch, Jing Zhang, and David A. Evans

Subjects
chemistry.chemical_classification, Ketone, Natural product, Molecular Structure, Polymers, Stereochemistry, Organic Chemistry, Absolute (perfumery), Stereoisomerism, Biochemistry, Aldehyde, Pyrrolidinones, Streptomyces, Adduct, chemistry.chemical_compound, chemistry, Polyol, Aldol reaction, Organic chemistry, Degradation (geology), Physical and Theoretical Chemistry
Abstract

[reaction: see text]. The C(8)-C(18) ethyl ketone and C(19)-C(28) aldehyde aflastatin A fragments were synthesized and coupled using a diastereoselective anti aldol reaction. This adduct was successfully converted into the C(9)-C(27) polyol degradation product of (-)-aflastatin A to confirm the relative and absolute stereochemistry of this region of the natural product.

Published
2005
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6. Complex Aldol Reactions for the Construction of Dense Polyol Stereoarrays: Synthesis of the C33−C36 Region of Aflastatin A

Author

Jason D. Burch, Frank Glorius, and David A. Evans

Subjects
Boron Compounds, inorganic chemicals, chemistry.chemical_classification, Molecular Structure, Chemistry, organic chemicals, Organic Chemistry, Diol, Stereoisomerism, Biochemistry, Acetonide, Aldehyde, Pyrrolidinones, Streptomyces, chemistry.chemical_compound, Polyol, Aldol reaction, polycyclic compounds, Organic chemistry, heterocyclic compounds, Physical and Theoretical Chemistry, Selectivity, Protecting group, Vicinal
Abstract

[reaction: see text]. Facial selectivity in the addition of boron enolates of alpha-oxygenated ketones to anti-disposed alpha,beta-bisalkoxy aldehydes is controlled by the aldehyde vicinal diol protecting group. Protection of the diol as an acetonide results in the exclusive formation of the anti-syn-anti stereoarray found in the C(33)-C(36) region of aflastatin A.

Published
2005
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7. Enantioselective total synthesis of callipeltoside A: two approaches to the macrolactone fragment

Author

Georg Jaeschke, David A. Evans, Jason D. Burch, and Essa Hu

Subjects
Olefin fiber, Natural product, Stereochemistry, Chemistry, Fragment (computer graphics), Organic Chemistry, Enantioselective synthesis, Total synthesis, Biochemistry, Combinatorial chemistry, Article, chemistry.chemical_compound, Aldol reaction, Drug Discovery, Side chain, Enantiomer
Abstract

The enantioselective total synthesis of callipeltoside A is described. Two syntheses of the macrolactone subunit are included: the first relies upon an Ireland–Claisen rearrangement to generate the trisubstituted olefin geometry and the second utilizes an enantioselective vinylogous aldol reaction for this purpose. Enantioselective syntheses of the sugar and chlorocyclopropane side chain fragments are also disclosed. The relative and absolute stereochemistry of this natural product was determined by fragment coupling with the two enantiomers of the side chain fragment.

Published
2012

8. ACS Medicinal Chemistry Reviews

Author

Joanne J. Bronson, Mark A. Murcko, Erin L. Cole, Lindsey R. Drake, Sanju Narayanan, Rajendra Uprety, Rangan Maitra, Scott Runyon, Wu Yang, James R. Corte, Joseph M. Luettgen, Zhi-Liang Wei, Danielle L. Aubele, Kelly A. Pike, Ramsay Beveridge, Patrick Cyr, Alex Skeldon, Li Wang, Jason D. Burch, Karin Worm, Jill Henault, Joachim Rudolph, Joanne J. Bronson

9. Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain

Author

Jason D. Burch and David A. Evans

Subjects
Cyclopropanes, Allylic rearrangement, Molecular Structure, Cyclopropanation, Organic Chemistry, Enantioselective synthesis, Stereoisomerism, Ether, Biochemistry, Combinatorial chemistry, Vinyl chloride, Anti-Bacterial Agents, chemistry.chemical_compound, chemistry, Callipeltoside A, Yield (chemistry), Side chain, Mannitol, Macrolides, Physical and Theoretical Chemistry
Abstract

[reaction: see text] The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-D-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.

Published
2001
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10. ChemInform Abstract: Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain

Author

Jason D. Burch and David A. Evans

Subjects
chemistry.chemical_compound, Allylic rearrangement, Callipeltoside A, chemistry, Cyclopropanation, Yield (chemistry), Enantioselective synthesis, Side chain, Organic chemistry, Ether, General Medicine, Combinatorial chemistry, Vinyl chloride
Abstract

The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-d-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.

Published
2010
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11. ChemInform Abstract: Enantioselective Total Synthesis of Callipeltoside A

Author

Georg Jaeschke, David A. Evans, Jason D. Burch, and Essa Hu

Subjects
inorganic chemicals, Callipeltoside A, Aldol reaction, Chemistry, organic chemicals, polycyclic compounds, Enantioselective synthesis, Organic chemistry, Total synthesis, General Medicine, Catalysis
Abstract

An asymmetric total synthesis of callipeltoside A has been accomplished highlighted by a catalytic enantioselective vinylogous aldol reaction and a boron-mediated anti-aldol reaction influenced by remote stereocontrol.

Published
2010
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13. Complex Aldol Reactions for the Construction of Dense Polyol Stereoarrays: Synthesis of the C33—C36 Region of Aflastatin A

Author

Frank Glorius, Jason D. Burch, and David A. Evans

Subjects
inorganic chemicals, chemistry.chemical_classification, Chemistry, organic chemicals, Diol, General Medicine, Acetonide, Aldehyde, chemistry.chemical_compound, Polyol, Aldol reaction, polycyclic compounds, Organic chemistry, heterocyclic compounds, Selectivity, Protecting group, Vicinal
Abstract

Facial selectivity in the addition of boron enolates of α-oxygenated ketones to anti-disposed α,β-bisalkoxy aldehydes is controlled by the aldehyde vicinal diol protecting group. Protection of the diol as an acetonide results in the exclusive formation of the anti-syn-anti stereoarray found in the C33−C36 region of aflastatin A.

Published
2005
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14. Synthesis and Confirmation of the Absolute Stereochemistry of the (-)-Aflastatin A C9—C27 Degradation Polyol

Author

David A. Evans, Jing Zhang, William C. Trenkle, and Jason D. Burch

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, Natural product, Ketone, chemistry, Aldol reaction, Polyol, Stereochemistry, Degradation (geology), Absolute (perfumery), General Medicine, Aldehyde, Adduct
Abstract

The C8−C18 ethyl ketone and C19−C28 aldehyde aflastatin A fragments were synthesized and coupled using a diastereoselective anti aldol reaction. This adduct was successfully converted into the C9−C27 polyol degradation product of (−)-aflastatin A to confirm the relative and absolute stereochemistry of this region of the natural product.

Published
2005
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15. Enantioselective total synthesis of callipeltoside A

Author

Essa Hu, Georg Jaeschke, Jason D. Burch, and David A. Evans

Subjects
inorganic chemicals, Stereochemistry, Anti-HIV Agents, Antineoplastic Agents, Biochemistry, Catalysis, Colloid and Surface Chemistry, Aldol reaction, Callipeltoside A, polycyclic compounds, Organic chemistry, Animals, chemistry.chemical_classification, Bicyclic molecule, Chemistry, organic chemicals, Enantioselective synthesis, Total synthesis, Stereoisomerism, General Chemistry, Anti-Bacterial Agents, Porifera, Stereoselectivity, Macrolides, Lactone
Abstract

An asymmetric total synthesis of callipeltoside A has been accomplished highlighted by a catalytic enantioselective vinylogous aldol reaction and a boron-mediated anti-aldol reaction influenced by remote stereocontrol.

Published
2002

16. One-Pot Synthesis of Benzofurans via Palladium-Catalyzed Enolate Arylation with o-Bromophenols.

Author

Christian Eidamshaus and Jason D. Burch

Subjects
*PALLADIUM (Game), *NATURAL products, *COMMERCIAL products, *RAW materials, *NATURAL foods industry
Abstract

A one-pot synthesis of benzofurans which utilizes a palladium-catalyzed enolate arylation is described. The process demonstrates broad substrate scope and provides differentially substituted benzofurans in moderate to excellent yields. The utility of the method is further demonstrated by the synthesis of the natural product eupomatenoid 6in three steps. [ABSTRACT FROM AUTHOR]

Published
2008
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17. ACS Medicinal Chemistry Reviews

Author

Joanne J. Bronson, Mark A. Murcko, Erin L. Cole, Lindsey R. Drake, Sanju Narayanan, Rajendra Uprety, Rangan Maitra, Scott Runyon, Wu Yang, James R. Corte, Joseph M. Luettgen, Zhi-Liang Wei, Danielle L. Aubele, Kelly A. Pike, Ramsay Beveridge, Patrick Cyr, Alex Skeldon, Li Wang, Jason D. Burch, Karin Worm, Jill Henault, Mark David Andrews, Marcel John de Groot, Kevin Neil Dack, Min Lu, Rachel L. Palte, Scott N. Mlynarski, Jason D. Shields, Oliver Schadt, Guangxiu Dai, Weiguo Xiang, Xin Han, Lijie Zhao, Shaomeng Wang, Thomas P. Stratton, Alexandre Mercier, Emma Abernathy, Jason Hudlicky, Lutete Peguy Khonde, Paul Jackson, Peter R. Hewitt, Oliver Barker, Matthew D. Helm, Xavier Jacq, Colin R. O'Dowd, Natalie Page, J. S. Shane Rountree, Timothy Harrison, Anmol Gulati, Xin Guo, Anton Delwig, Noriko Ishisoko, Robert A. Blake, Jose Raul Montero Bastidas, Abdellatif El Marrouni, Maria Irina Chiriac, Thomas Struble, Dipannita Kalyani, Jeffrey A. Dodge, Michael J. Chalmers, Howard Broughton, Alfonso Espada, Joshua A. Lees, Seungil Han, Gene M. Dubowchik, Robe, Joanne J. Bronson, Mark A. Murcko, Erin L. Cole, Lindsey R. Drake, Sanju Narayanan, Rajendra Uprety, Rangan Maitra, Scott Runyon, Wu Yang, James R. Corte, Joseph M. Luettgen, Zhi-Liang Wei, Danielle L. Aubele, Kelly A. Pike, Ramsay Beveridge, Patrick Cyr, Alex Skeldon, Li Wang, Jason D. Burch, Karin Worm, Jill Henault, Mark David Andrews, Marcel John de Groot, Kevin Neil Dack, Min Lu, Rachel L. Palte, Scott N. Mlynarski, Jason D. Shields, Oliver Schadt, Guangxiu Dai, Weiguo Xiang, Xin Han, Lijie Zhao, Shaomeng Wang, Thomas P. Stratton, Alexandre Mercier, Emma Abernathy, Jason Hudlicky, Lutete Peguy Khonde, Paul Jackson, Peter R. Hewitt, Oliver Barker, Matthew D. Helm, Xavier Jacq, Colin R. O'Dowd, Natalie Page, J. S. Shane Rountree, Timothy Harrison, Anmol Gulati, Xin Guo, Anton Delwig, Noriko Ishisoko, Robert A. Blake, Jose Raul Montero Bastidas, Abdellatif El Marrouni, Maria Irina Chiriac, Thomas Struble, Dipannita Kalyani, Jeffrey A. Dodge, Michael J. Chalmers, Howard Broughton, Alfonso Espada, Joshua A. Lees, Seungil Han, Gene M. Dubowchik, and Robe

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