Champaign, IL, United States
Champaign, IL, United States

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Lee W.,Chosun University | Snyder S.E.,University of Illinois at Urbana - Champaign | Volkers P.I.,University of Illinois at Urbana - Champaign | Pirkle W.H.,University of Illinois at Urbana - Champaign | And 5 more authors.
Tetrahedron | Year: 2011

Chiral stationary phases were synthesized and their ability to separate racemic precursors from which they were derived was assessed. Taken in conjunction with homochiral recognition previously observed in the solid state, the results of this study reveal that a geometrically controlling π-π interaction has a profound influence on molecular recognition. © 2011 Elsevier Ltd. All rights reserved.


Miller C.P.,Radius Health Inc. | Shomali M.,Radius Health Inc. | Lyttle C.R.,Radius Health Inc. | O'dea L.S.L.,Radius Health Inc. | And 12 more authors.
ACS Medicinal Chemistry Letters | Year: 2011

This report describes the discovery of RAD140, a potent, orally bioavailable, nonsteroidal selective androgen receptor modulator (SARM). The characterization of RAD140 in several preclinical models of anabolic androgen action is also described. © 2010 American Chemical Society.


Zeng C.-M.,Obiter Research | Kerrigan S.A.,Obiter Research | Katzenellenbogen J.A.,University of Illinois at Urbana - Champaign | Slocum C.,Radius Health Inc. | And 5 more authors.
Tetrahedron Letters | Year: 2010

An efficient synthesis of the non-proteinogenic amino acid (2R,3S)-4,4,4-trifluoro(OBn)-threonine is described. Starting with commercially available (S)-Garner's aldehyde, the desired amino acid was prepared as its hydrochloride salt in five steps and an overall yield of 33% (59% based on recovered starting material). The utility of this unusual amino acid was demonstrated by its elaboration into a potent and selective androgen. © 2010 Elsevier Ltd. All rights reserved.


Sulfonamide heterocycles, specifically 3-acylindoles, undergo a deprotection/alkylation sequence in the presence of an appropriate alcohol when cesium carbonate or potassium carbonate and a phase-transfer catalyst are utilized. The outcome of the one-pot protocol was found to be significantly dependent on both the alcohol and sulfonamide heterocycle employed. Strictly anhydrous conditions are not necessary for this protocol. © Georg Thieme Verlag Stuttgart · New York.


Denton J.R.,Obiter Research
Synthetic Communications | Year: 2011

A protocol has been developed to purify 9-(trifluoroacetyl)anthracene from anthracene, the major impurity associated in its synthesis. The protocol utilizes a chemoselective thermal Diels-Alder reaction, employing maleic anhydride as the dienophile. The resulting Diels-Alder adduct can then be removed by extractive workup followed by recrystallization to give 9-(trifluoroacetyl)anthracene with ≥99% chemical purity. © 2011 Taylor & Francis Group LLC.

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