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199 results on '"Dolling, Ulf H."'

1. Practical synthesis of the new carbapenem antibiotic ertapenem sodium

Author

Williams, J. Micheal, Brands, Karel M.J., Skerlj, Renato T., Jobson, Ronald B., Marchesini, George, Conrad, Karen M., Pipik, Brenda, Savary, Kimberly A., Tsay, Fuh-Rong, Houghton, Peter G., Sidler, D. Richard, Dolling, Ulf-H., DiMichele, Lisa M., and Novak, Thomas J.

Subjects
Amino compounds -- Chemical properties, Carbonyl compounds -- Chemical properties, Carboxylic acids -- Chemical properties, Biological sciences, Chemistry
Abstract

A practical synthesis for the large-scale production of the new carbapenem anitbiotic, [4R,5S,6S]-3-[[(3S,5S)-5-[[(3-Carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium salt (ertapenem sodium) is developed. The strategy and discoveries leading to practical synthesis for the new antibiotic ertapenem sodium allowing production on multi-kilogram scale are described.

Published
2005

2. Theoretical study of the vinyl allene oxide to cyclopent-2-en-1-one rearrangement: mechanism, torquoselectivity and solvent effects

Author

Lopez, Carlos Silva, Faza, Olalla Nieto, York, Darrin M., de Lera, Angel R., Dolling, Ulf H., McMasters, Daniel R., Kress, Michael H., and McNamara, James M.

Subjects
Transition state (Chemistry) -- Observations, Chemistry, Organic -- Research, Biological sciences, Chemistry
Abstract

The characterization of two distinct competing mechanistic pathways for the rearrangement of vinyl allene oxides to cyclopent-2-en-1-ones is described. The concerted transition structure is shown as a monorotatory ring closure with concomitant epoxide ring opening

Published
2004

3. Nortricyclyl-norbornenyl cation system accessed by carbene fragmentation

Author

Moss, Robert A., Sauers, Ronald R., Madni, Mahvash, McLaughlin, Kathleen, Brower, Mark, Sturr, Michael, Dolling, Ulf H., McMasters, Daniel R., Kress, Michael H., and McNamara, James M.

Subjects
Cations -- Usage, Chemistry, Organic -- Research, Biological sciences, Chemistry
Abstract

An S(subN)i-like process yielding nortricyclyl chloride and causing fragmentation of nortricyclyloxychlorocarbene in pentane is described. The results are rationalized by invoking nortricyclyl chloride and norbornenyl chloride ion pairs and methanol-solvated nortricyclyl cations.

Published
2004

4. Stereoselective synthesis of a potent thrombin inhibitor by a novel P2-P3 lactone ring opening

Author

Nelson, Todd D, LeBlond, Carl R, Frantz, Doug E., Matty, Louis, Mitten, Jeffrey V., Weaver, Damian G., Moore, Jeffrey C., Kim, Jaehon M., Boyd, Russell, Pei-Yi, Kim, Gbewonyo, Kodzo, Brower, Mark, Sturr, Michael, McLaughlin, Kathleen, McMasters, Daniel R., Kress, Michael H., McNamara, James M., and Dolling, Ulf H.

Subjects
Stereochemistry -- Observations, Lactones -- Research, Lactones -- Chemical properties, Thrombin -- Research, Thrombin -- Chemical properties, Chemistry, Organic -- Research, Biological sciences, Chemistry
Abstract

The framework for a potent thrombin inhibitor was obtained by the ring opening of a diastereomerically pure bicyclic lactone with an orthogonally protected bisbenzylic amine. In addition, two efficient complementary syntheses of the diasteromerically pure lactone highlighted the synthesis.

Published
2004

5. Practical asymmetric synthesis of aprepitant, a potent human NK-1 receptor antagonist, via a stereoselective Lewis acid-catalyzed trans acetalization reaction

Author

Zhao, Matthew M., McNamara, James M., Ho, Guo-Jie, Emerson, Khateeta M., Song, Zhiguo J., Tschaen, David M., Brands, Karel M. J., Dolling, Ulf-H, Grabowski, Edward J. J., and Reider, Paul J.

Subjects
Chemistry, Organic -- Research, Acids -- Physiological aspects, Tachykinins -- Physiological aspects, Stereochemistry -- Research, Catalysis -- Physiological aspects, Chemical reactions -- Analysis, Biological sciences, Chemistry
Abstract

Research has been conducted on the potent mammalian tachykinin substance P receptor antagonist, aprepitant. The synthesis of this antagonist is described.

Published
2002

6. Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem

Author

Brands, Karel M. J., Jobson, Ronald B., Conrad, Karen M., Williams, J. Michael, Pipik, Brenda, Cameron, Mark, Davies, Antony J., Houghton, Peter G., Ashwood, Michael S., Cottrell, Ian F., Reamer, Robert A., Kennedy, Derek J., Dolling, Ulf-H., and Reider, Paul J.

Subjects
Chemistry, Organic -- Research, Amines -- Physiological aspects, Carbon -- Physiological aspects, Antibiotics -- Physiological aspects, Chemical reactions -- Analysis, Biological sciences, Chemistry
Abstract

Research has been conducted on the 2-aminocarbonylpyrrolidin-4-ylthio compounds. The synthesis of these compounds which contain ertapenem side chain has been carried out and the results are reported.

Published
2002

7. Practical asymmetric synthesis of an endothelin receptor antagonist

Author

Song, Zhiguo J., Zhao, Mangzhu, Desmond, Richard, Devine, Paul, Tschaen, David M., Tillyer, Richard, Frey, Lisa, Heid, Richard, Xu, Feng, Foster, Bruce, Li, Jing, Reamer, Robert, Volante, Ralph, Grabowski, Edward J.J., Dolling, Ulf H., Reider, Paul J., Okada, Shigemitsu, Kato, Yoshiaki, and Mano, Eiichi

Subjects
Chemistry, Organic -- Research, Endothelin -- Research, Biological sciences, Chemistry
Abstract

The article examines the endothelin receptor antagonist asymmetric synthesis. A construction of the pyridine-fused cyclopentane ring with three chiral centers is discussed.

Published
1999

8. Methoxymethylation of alcohols, phenols, and avermectin aglycones using MOM-2-pyridylsulfide

Author

Marcune, Benjamin F., Karady, Sandor, Dolling, Ulf-H., and Novak, Thomas J.

Subjects
Phenols -- Research, Alcohol -- Research, Biological sciences, Chemistry
Abstract

A study was conducted to analyze the methoxymethylation of phenols, alcohols and avermectin aglycones. Methoxymethyl moiety-2-pyridylsulfide (MOM-ON) was utilized to carry out the analysis. The Zorbx SB phenyl column was utilized to perform high performance liquid chromatography. Experimental results indicated that effectiveness of MOM-ON as a methoxymethylating reagent of alcohols and phenols.

Published
1999

10. Mild aryl ether formation in the semisynthesis of the novel macrolide immunosuppressant L-732,531

Author

Brands, Karel M. Jos, Dolling, Ulf-H., Jobson, Ronald B., Marchesini, George, Reamer, Robert A., and Williams, J. Michael

Subjects
Alcohols -- Research, Immunosuppression -- Research, Macrolide antibiotics -- Research, Biological sciences, Chemistry
Abstract

A study was conducted to characterize the preparation of bismuthane and its coupling with the macrolide alcohol to produce an immunosuppressant after deprotection. Iodometric titration was carried out to determine the quality of the benzoyl peroxide. Results indicated that a tert-butyldimethylsilyl protecting group supported the optimal balance between ease of introduction in bismuthane and removal from the macrolide.

Published
1998

11. Practical synthesis of anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem L-742,728

Author

Yasuda, Nobuyoshi, Huffman, Mark A., Ho, Guo-Jie, Xavier, Lyndon C., Yang, Chunhua, Emerson, Khateeta M., Tsay, Fuh-Rong, Li, Yulan, Kress, Michael H., Rieger, Dale L., Karady, Sandor, Sohar, Paul, Abramson, Newton L., DeCamp, Ann E., Mathre, David J., Douglas, Alan W., Dolling, Ulf-H., Grabowski, Edward J.J., and Reider, Paul J.

Subjects
Staphylococcus aureus -- Research, Methicillin -- Research, Antibacterial agents -- Structure-activity relationships, Biological sciences, Chemistry
Abstract

Research was conducted to confirm anti-methicillin-resistant Staphylococcus aureus activity on carbapenems, specifically L-742,728, having aromatic substituents at the 3-position. The study utilized the Suzuki-Miyaura crosscoupling between dicationic boronic acid 20 and in situ prepared carbapenem vinyl triflate 26 as the key reaction. Results indicated synthesis of the carbapenem in 31-36% yield over six steps from the diazo intermediate 2.

Published
1998

12. Stereoselective conjugate addition reactions of alpha,beta-unsaturated tert-butyl esters with aryllithium reagents

Author

Frey, Lisa F., Tillyer, Richard D., Caille, Alain-Sebastien, Tschaen, David M., Dolling, Ulf-H., Grabowski, J.J., and Reider, Paul J.

Subjects
Lithium -- Research, Esters -- Research, Enantiomers -- Research, Biological sciences, Chemistry
Abstract

Aryllithium reagents were observed to react rapidly and efficiently with beta-aryl-alpha,beta-unsaturated tert-butyl esters having a chiral imidazolidine or oxazolidine to produce 1,4-addition products in high yield and optical purity. The process is practical and employs readily available and inexpensive chiral auxiliaries, and can be employed to produce a broad range of structurally complex chiral beta,beta-diaryl propanoates.

Published
1998

13. Sequential dehydrogenation of 3-keto-4-azasteroids. The reaction of ene-lactams with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)

Author

Williams, J. Michael, Marchesini, George, Reamer, Robert A., Dolling, Ulf-H., and Grabowski, Edward J.J.

Subjects
Dehydrogenation -- Research, Steroids (Drugs) -- Analysis, Biological sciences, Chemistry
Abstract

A method has been devised for the controlled and systematic dehydrogenation of 3-keto-4-azasteroids. This is done by using electrochemical oxidation after which a reaction of ene-lactams with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is demonstrated. The reaction produces highly unsaturated azasteroids which do not react readily with DDQ even when the following tautomerization to the delta(super 5)-3-keto-4-azasteroid is slow. Thus the problem of the product getting easily oxidized is solved.

Published
1995

14. Asymmetric synthesis of MK-0499

Author

Tschaen, David M., Abramson, Lee, Cai, Dongwei, Desmond, Richard, Dolling, Ulf-H, Frey, Lisa, Karady, Sandor, Shi, Yao-Jun, and Verhoeven, Thomas R.

Subjects
Organic compounds -- Synthesis, Ruthenium -- Usage, Stereochemistry -- Analysis, Biological sciences, Chemistry
Abstract

A potent potassium channel blocker, MK-0499, has been synthesized from a ketone through asymmetric synthesis involving two stereoselective reactions. The primary intermediate was synthesized by enantioselective hydrogenation of an enamide using ruthenium catalyst and the alcohol stereochemistry was developed by reduction of ketone, initiated by oxazaborolidine. The addition of 1 mol of IPA to the reaction enhances the diasteroselectivity of the reduction procedure.

Published
1995

17. A novel crystallization-induced diastereomeric transformation based on a reversible carbon-sulfur bond formation. Application to the synthesis of a [gamma]-secretase inhibitor

Author

Davies, Antony J., Scott, Jeremy P., Bishop, Brian C., Brands, Karel M.J., Dormer, Peter G., Dolling, Ulf-H., Gibb, Andrew D., Brewer, Sarah E., DaSilva, Jimmy O., Hammond, Deborah C., and Lieberman, David R.

Subjects
Carbon compounds -- Chemical properties, Crystallization -- Analysis, Benzene -- Chemical properties, Sulfur compounds -- Chemical properties, Biological sciences, Chemistry
Abstract

An efficient process is described for the preparation of [gamma]-secretase inhibitor. The operation is a highly selective and practical, crystallization-driven transformation for the conversion of a mixture of tertiary benzylic alcohols into the desired sulfide diastereomer, which is based on a reversible carbon-sulfur bond formation under acidic conditions.

Published
2007

18. A practical synthesis of a [gamma]-secretase inhibitor

Author

Scott, Jeremy P., Lieberman, David R., Beureux, Olivier M., Brands, Karel M.J., Davies, Antony J., Gibson, Andrew W., Hammond, Deborah C., McWilliams, Chris J., Stewart, Gavin W., Wilson, Robert D., and Dolling, Ulf-H.

Subjects
Chemical synthesis -- Analysis, Biological sciences, Chemistry
Abstract

A practical and scaleable synthesis of the [gamma]-secretase inhibitor, which consists of a central trisubtituted cyclohexane core with appended propionic acid, 2-5-difluorophenyl, and 4-chlorophenylsulfonyl moieties, is presented.

Published
2007

19. Practical asymmetric synthesis of a gamma-secretase inhibitor exploiting substrate-controlled intramolecular nitrile oxide-olefin cycloaddition

Author

Scott, Jeremy P., Oliver, Steven F., Brands, Karel M.J., Brewer, Sarah E., Davies, Antony J., Gibb, Andrew D., Hands, David, Keen, Stephen P., Sheen, Faye J., Reamer, Robert A., Wilson, Robert D., and Dolling, Ulf-H.

Subjects
Ring formation (Chemistry) -- Analysis, Nitriles -- Chemical properties, Olefins -- Chemical properties, Biological sciences, Chemistry
Abstract

A practical asymmetric synthesis of the gamma-secretase inhibitor (-)-1 that is amenable to multikilogram operation is reported. Kilogram quantities of the targeted drug candidate (-)-1 are obtained, without recourse to chromatography, by way of 10 isolated intermediates and in 13% overall yield.

Published
2006

20. Synthesis of a NO-releasing prodrug of rofecoxib

Author

Engelhardt, F. Conrad, Yao-Jun Shi, Cowden, Cameron J., Conlon, David A., Pipik, Brenda, Zhou, George, McNamara, James M., and Dolling, Ulf-H.

Subjects
Rofecoxib -- Research, Antiarthritic agents -- Research, Biological sciences, Chemistry
Abstract

A newly developed synthesis of a NO-releasing prodrug of refecoxib is presented. The synthesis of the NO-COXIB drug is completed through two alternate end-game strategies designed to control impurity and byproduct level.

Published
2006

21. Practical asymmetric synthesis of a non-peptidic alpha(sub nu)beta3 antagonist

Author

Keen, Stephen P., Cowden, Cameron J., Bishop, Brian C., Brands, Karel M.J., Davies, Antony J., Stewart, Gavin W, Liebermann, David R., and Dolling, Ulf H.

Subjects
Anhydrides -- Chemical properties, Chirality -- Research, Aldehydes -- Chemical properties, Biological sciences, Chemistry
Abstract

The development of a practical and highly convergent synthesis of an alpha(sub nu)beta3 antagonist is described. Highlights of this synthesis include a one-pot alkylation/cyclization to construct the seven-membered ring of the pyrido[2,3-b]-azepine moiety, highly efficient Suzuki coupling to attach the propionaldehyde side-chain, and enantioselective desymmetrization of a 3-substituted glutaric anhydride to set the sole chiral center.

Published
2005

22. Intramolecular aromatic 1,5-hydrogen transfer in free radical reactions. 1. Unprecedented rearrangements in Pschorr cyclization, Sandmeyer, and hydro-, hydroxy-, and iododediazoniation reactions

Author

Karady, Sandor, Abramson, N. Lee, Dolling, Ulf-H., Douglas, Alan W., McManemin, Gregory J., and Marcune, Benjamin

Subjects
Free radical reactions -- Analysis, Benzophenone -- Research, Rearrangements (Chemistry) -- Analysis, Chemistry
Abstract

The benzophenone radicals obtained from the respective diazonium salts undergo a vigorous 1,5-hydrogen transfer resulting in a partial equilibrium among the radicals. Rearrangement of the initially formed radicals by 1,5-hydrogen transfer is the mechanism of the Pschorr cyclization which produces two isomeric fluorenones. A 1,5-hydrogen transfer also occurs in the hydrodediazoniation, Sandmeyer and iododediazoniation reactions.

Published
1995

27. Development of a Scaleable Synthesis of a Partial Nicotinic Acid Receptor Agonist

Author

Wilson, Robert D., primary, Cleator, Ed, additional, Ashwood, Michael S., additional, Bio, Matthew M., additional, Brands, Karel M. J., additional, Davies, Antony J., additional, Dolling, Ulf-H., additional, Emerson, Khateeta M., additional, Gibb, Andrew D., additional, Hands, David, additional, McKeown, Arlene E., additional, Oliver, Steven F., additional, Reamer, Robert A., additional, Sheen, Faye J., additional, Stewart, Gavin W., additional, and Zhou, George X., additional

Published
2009
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28. Development of a Phase Transfer Catalyzed Asymmetric Synthesis for an Estrogen Receptor Beta Selective Agonist

Author

Scott, Jeremy P., primary, Ashwood, Michael S., additional, Brands, Karel M. J., additional, Brewer, Sarah E., additional, Cowden, Cameron J., additional, Dolling, Ulf-H., additional, Emerson, Khateeta M., additional, Gibb, Andrew D., additional, Goodyear, Adrian, additional, Oliver, Steven F., additional, Stewart, Gavin W., additional, and Wallace, Debra J., additional

Published
2007
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29. A Novel Crystallization-Induced Diastereomeric Transformation Based on a Reversible Carbon−Sulfur Bond Formation. Application to the Synthesis of a γ-Secretase Inhibitor

Author

Davies, Antony J., primary, Scott, Jeremy P., additional, Bishop, Brian C., additional, Brands, Karel M. J., additional, Brewer, Sarah E., additional, DaSilva, Jimmy O., additional, Dormer, Peter G., additional, Dolling, Ulf-H., additional, Gibb, Andrew D., additional, Hammond, Deborah C., additional, Lieberman, David R., additional, Palucki, Michael, additional, and Payack, Joseph F., additional

Published
2007
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32. Practical Asymmetric Synthesis of a γ-Secretase Inhibitor Exploiting Substrate-Controlled Intramolecular Nitrile Oxide−Olefin Cycloaddition

Author

Scott, Jeremy P., primary, Oliver, Steven F., additional, Brands, Karel M. J., additional, Brewer, Sarah E., additional, Davies, Antony J., additional, Gibb, Andrew D., additional, Hands, David, additional, Keen, Stephen P., additional, Sheen, Faye J., additional, Reamer, Robert A., additional, Wilson, Robert D., additional, and Dolling, Ulf-H., additional

Published
2006
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33. Synthesis of a NO-Releasing Prodrug of Rofecoxib

Author

Engelhardt, F. Conrad, primary, Shi, Yao-Jun, additional, Cowden, Cameron J., additional, Conlon, David A., additional, Pipik, Brenda, additional, Zhou, George, additional, McNamara, James M., additional, and Dolling, Ulf-H., additional

Published
2005
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42. Stereoselective Synthesis of a Potent Thrombin Inhibitor by a Novel P2−P3 Lactone Ring Opening

Author

Nelson, Todd D., primary, LeBlond, Carl R., additional, Frantz, Doug E., additional, Matty, Louis, additional, Mitten, Jeffrey V., additional, Weaver, Damian G., additional, Moore, Jeffrey C., additional, Kim, Jaehon M., additional, Boyd, Russell, additional, Kim, Pei-Yi, additional, Gbewonyo, Kodzo, additional, Brower, Mark, additional, Sturr, Michael, additional, McLaughlin, Kathleen, additional, McMasters, Daniel R., additional, Kress, Michael H., additional, McNamara, James M., additional, and Dolling, Ulf H., additional

Published
2004
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50. Practical Asymmetric Synthesis of Aprepitant (I), a Potent Human NK-1 Receptor Antagonist, via a Stereoselective Lewis Acid Catalyzed trans Acetalization Reaction.

Author

Zhao, Matthew, primary, McNamara, James M., additional, Ho, Guo-Jie, additional, Emerson, Khateeta M., additional, Song, Zhiguo J., additional, Tschaen, David M., additional, Brands, Karel M. J., additional, Dolling, Ulf-H, additional, Grabowski, Edward J. J., additional, and Reider, Paul J., additional

Published
2003
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