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2. Research, teaching, and professional development at a comprehensive university

Author

Ball, David B., Wood, Mike, Lindsley, Craig, Mollard, Paul, Buzard, D. J., Vivian, Randy, Mahoney, Max, and Taft, Benjamin R.

Subjects
College students -- Study and teaching, Chemical research, Chemistry, Education, Science and technology, California State University Chico -- Curricula
Abstract

The convergent synthesis of borrelidin is an actively pursued research project by undergraduate chemistry students at Chico State and the varied laboratory techniques, chemistry and required spectral analysis give them a rich undergraduate research experience. Each student who has worked on borrelidin has made a positive contribution to the project with most helping to move this project towards completion.

Published
2004

11. Synthesis of a Broad Array of Highly Functionalized, Enantiomerically Pure Cyclohexanecarboxylic Acid Derivatives by Microbial Dihydroxylation of Benzoic Acid and Subsequent Oxidative and Rearrangement Reactions

Author

Myers, A. G., Siegel, D. R., Buzard, D. J., and Charest, M. G.

Abstract

We have found that the 1,2-dihydroxylation of benzoic acid with Alcaligenes eutrophus strain B9, first reported in 1971 by Reiner and Hegeman, is readily adapted for the preparation of tens to hundreds of grams of (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid of >95% ee. This unique substrate undergoes many specific oxidative and rearrangement processes. Among these are transformations of unanticipated chemical novelty and many products that have not been previously described.

Published
2001

17. ChemInform Abstract: Reductions of Aryl Perfluorosulfonates with Dimethylamine‐borane (Me2NH×BH3) Catalyzed by Pd(0): An Operationally Simple, Inexpensive, and General Protocol.

Author

Lipshutz, Bruce H., Buzard, D. J., and Vivian, Randall W.

Abstract

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Published
1999
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18. Complementary asymmetric routes to (R)-2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate.

Author

Schrader TO, Johnson BR, Lopez L, Kasem M, Gharbaoui T, Sengupta D, Buzard D, Basmadjian C, and Jones RM

Subjects
Acetates chemistry, Acetates pharmacology, Catalysis, Fingolimod Hydrochloride, Indoles chemistry, Indoles pharmacology, Molecular Structure, Propylene Glycols chemical synthesis, Propylene Glycols chemistry, Propylene Glycols pharmacology, Pyrroles chemistry, Pyrroles pharmacology, Receptors, Lysosphingolipid agonists, Sphingosine analogs & derivatives, Sphingosine chemical synthesis, Sphingosine chemistry, Sphingosine pharmacology, Stereoisomerism, Acetates chemical synthesis, Indoles chemical synthesis, Pyrroles chemical synthesis
Abstract

Two distinct and scalable enantioselective approaches to the tricyclic indole (R)-2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate, an important synthon for a preclinical S1P(1) receptor agonist, are reported. Route 1 employs a modified version of Smith's modular 2-substituted indole synthesis as the key transformation. Route 2 involves a highly enantioselective CuH-catalyzed 1,4-hydrosilylation as the stereodefining step. Both routes can be performed without chromatography to provide multigram quantities of the tricycle in ≥98% ee.

Published
2012
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19. Discovery and characterization of potent and selective 4-oxo-4-(5-(5-phenyl-1,2,4-oxadiazol-3-yl)indolin-1-yl)butanoic acids as S1P₁ agonists.

Author

Buzard D, Han S, Thoresen L, Moody J, Lopez L, Kawasaki A, Schrader T, Sage C, Gao Y, Edwards J, Barden J, Thatte J, Fu L, Solomon M, Liu L, Al-Shamma H, Gatlin J, Le M, Xing C, Espinola S, and Jones RM

Subjects
Animals, Butyrates pharmacokinetics, Disease Models, Animal, Dogs, Dose-Response Relationship, Drug, Drug Discovery, Drug Evaluation, Preclinical, Haplorhini, High-Throughput Screening Assays, Humans, Immunosuppressive Agents pharmacokinetics, Indoles pharmacokinetics, Male, Mice, Mice, Inbred BALB C, Nerve Tissue Proteins chemistry, Oxadiazoles pharmacokinetics, RNA-Binding Proteins chemistry, Rats, Rats, Sprague-Dawley, Structure-Activity Relationship, Substrate Specificity, Autoimmune Diseases drug therapy, Butyrates chemical synthesis, Butyrates pharmacology, Immunosuppressive Agents chemical synthesis, Immunosuppressive Agents pharmacology, Indoles chemical synthesis, Indoles pharmacology, Lymphocytes metabolism, Nerve Tissue Proteins agonists, Oxadiazoles chemical synthesis, Oxadiazoles pharmacology, RNA-Binding Proteins agonists
Abstract

S1P(1) receptor driven lymphopenia has proven utility in the treatment of an array of autoimmune disease states. As a part of our efforts to develop potent and selective S1P(1) receptor agonists, we have identified a novel chemical series of 4-oxo-4-(5-(5-phenyl-1,2,4-oxadiazol-3-yl)indolin-1-yl)butanoic acid S1P(1) receptor agonists., (Copyright © 2011 Elsevier Ltd. All rights reserved.)

Published
2011
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