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Your search keyword '"Wallace, Grier A."' showing total 23 results
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23 results on '"Wallace, Grier A."'

1. Multigram synthesis of the C29-C51 subunit and completion of the total syntheis of altohyrtin C (spongistatin 2)

Author

Heathcock, Clayton H., McLaughlin, Mark, Medina, Jesus, Hubbs, Jedd L., Wallace, Grier A, Scott, Robert C., Claffey, Michele M., Hayes, Christopher J, and Ott, Gregory R.

Subjects
Organometallic compounds -- Research, Organometallic compounds -- Chemical properties, Antineoplastic antibiotics -- Research, Chemistry
Abstract

A multigram synthesis of a protected version of the C29-C51 subunit and the methodology for the union of this intermediate with the C1-C28 fragment to achieve the natural product is reported. By this route a total of 0.25 grams of the marine natural product was prepared.

Published
2003

2. Stereoselective total syntheses and reassignment of stereochemistry of the freshwater cyanobacterial haptatoxins cylindrospermopsin and 7-epicylindrospermopsin

Author

Heintzelman, Geoffrey R., Fang, Wen-Kui, Keen, Stephen P., Wallace, Grier A., and Weinreb, Stevn M.

Subjects
Chemical research -- Analysis, Stereochemistry -- Research, Cyanobacteria -- Physiological aspects, Toxins -- Physiological aspects, Ring formation (Chemistry) -- Physiological aspects, Pyridine -- Physiological aspects, Chemistry
Abstract

Research has been conducted on the cyanobacterial haptatoxins cylindrospermopsin. The structure of this cylindrospermopsin has been investigated and the results of its stereoselective synthesis which starts with 4-methoxypyridine are discussed.

Published
2002

3. Further studies of the Daphniphyllum alkaloid polycyclization cascade

Author

Wallace, Grier A. and Heathcock, Clayton H.

Subjects
Alkaloids -- Research, Natural products -- Research, Diels-Alder reaction -- Analysis, Ring formation (Chemistry) -- Analysis, Biological sciences, Chemistry
Abstract

The Daphniphyllum alkaloid polycyclization tolerates various alkyl substitution in the dienophile but exhibits decline in rate with electron deficient dienophiles. Furthermore, the structure of the 2-azadiene is critical as well as the cyclopentyl ring and quternary and tertiary carbon centers of the diol for cyclization.

Published
2001

4. Synthesis of the C29-C44 portion of spongistatin 1 (altohyrtin A)

Author

Wallace, Grier A., Scott, Robert W., and Heathcock, Clayton H.

Subjects
Lactones -- Research, Macrolide antibiotics -- Research, Chemical reactions -- Analysis, Organic compounds -- Synthesis, Biological sciences, Chemistry
Abstract

Research describes two synthetic routes for the synthesis of the C29-C44 part of the spongistatin 1 macrocyclic lactone. The first methods employs Claisen rearrangement, Mukaiyama coupling, and cyclization steps. The second procedure is based on the C-glycosidation, condensation, and ketalization. The yields are 2.45 and 13.2%, respectively.

Published
2000

6. Stereoselective total synthesis of the cyanobacterial hepatotoxin 7-epicylindrospermopsin: Revision of the stereochemistry of cylindrospermopsin

Author

Heintzelman, Geoffrey R., Wen-Kui Fang, Keen, Stephen P., Wallace, Grier A., and Weinreb, Steven M.

Subjects
Algae -- Health aspects, Bacteria -- Research, Drinking water -- Safety and security measures, Chemistry
Abstract

Research investigating the chemical reactions caused by the blue-green alga called Cylindrospermopsin raciborskii found in the waters of Palm Island, Australia, is presented. Particular attention is given to the stereochemistry of the alga producing a toxic substance.

Published
2001

9. Scalable synthesis and isolation of the four stereoisomers of methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate, useful intermediates for the synthesis of S1P1 receptor agonists

Author

Wallace, Grier A., Gordon, Thomas D., Hayes, Martin E., Konopacki, Donald B., Fix-Stenzel, Shannon R., Xiaolei Zhang, Grongsaard, Pintipa, Cusak, Kevin P., Schaffter, Lisa M., Henry, Rodger F., and Stoffel, Robert H.

Subjects
Chemical synthesis -- Research, Stereoisomers -- Research, Carboxylic acids -- Research, Biological sciences, Chemistry
Abstract

The scalable synthesis and isolation of each of the four stereoisomers of methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate in gram quantities is described. The utility of this method is shown by the synthesis of ((1R,3E)-amino-3-(4-octylphenyl)cyclopentyl)methanol in 7 steps.

Published
2009

10. Scalable Synthesis of ABBV-105 Enabled by Suzuki Coupling with Low Pd Loading, Ru-Catalyzed Asymmetric Hydrogenation, and Acylation Using Impinging Jet

Author

Cardinal-David, Benoit, Shekhar, Shashank, Phillips, Eric M., Swift, Elizabeth C., Kotecki, Brian, Ickes, Andrew R., Storer, Gregory E., Caspi, Daniel D., Verma, Anuj, Moschetta, Eric G., Tao, Daniel, Morrill, Westin H., Bellettini, John R., Nordstrom, Fredrik L., Mattei, Alessandra, Springer, Kirsten, Qiu, Haixiao, Bien, Jeffrey T., Manjrekar, Onkar, Henry, Rodger F., Wallace, Grier A., Schaffter, Lisa, and Voight, Eric A.

Abstract

Evolution of a synthetic process to prepare ABBV-105, a Bruton’s tyrosine kinase (BTK)-inhibitor, on multikilogram scale is described. The first-generation route utilized chiral resolution of the penultimate intermediate (7). Either Bartoli or Leimgruber–Batcho indole synthesis was used to prepare the key intermediate, indole boronate ester (23). As the demand for the API increased, the first-generation route was found to be low-yielding and expensive. It required column chromatography, had multiple alerting structures from the mutagenic impurity assessment, and suffered from lack of robustness. In the second-generation route a novel Ru-catalyzed asymmetric hydrogenation of 1,2,5,6-tetrahydropyridine (21) was developed to establish the stereocenter. Compound 21was accessed via Suzuki coupling of 23, prepared by Friedel–Crafts acylation, with vinyl bromide (24) in the presence of very low loading of a Pd catalyst (0.15 mol % Pd). Finally, the penultimate intermediate (7) was coupled with acryloyl chloride using an impinging jet to prepare the API. Detailed kinetic and mechanistic work was conducted to control the persistent impurities formed in the API step. The second-generation route was robust, chromatography-free and high-yielding with low mutagenic liability.

Published
2024
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11. Design and synthesis of tricyclic cores for kinase inhibition

Author

Van Epps, Stacy, Fiamengo, Bryan, Edmunds, Jeremy, Ericsson, Anna, Frank, Kristine, Friedman, Michael, George, Dawn, George, Jonathan, Goedken, Eric, Kotecki, Brian, Martinez, Gloria, Merta, Philip, Morytko, Michael, Shekhar, Shashank, Skinner, Barbara, Stewart, Kent, Voss, Jeffrey, Wallace, Grier, Wang, Lu, and Wishart, Neil

Published
2013
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