366014-79-1Relevant academic research and scientific papers
Addition of aryllithiums to an 11-oxo-steroid
Lecomte, Vincent,Foy, Nicolas,Le Bideau, Franck,Stéphan, Elie,Jaouen, Gérard
, p. 5409 - 5411 (2001)
The addition of aryllithiums to an 11-oxo-steroid is possible in non-polar medium and at room temperature. A series of protected 11α-aryl-11β-hydroxy-androsten-diones have been prepared.
COMPLEX AND STRUCTURALLY DIVERSE COMPOUNDS
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, (2015/12/20)
The invention provides a novel, general, and facile strategy for the creation of small molecules with high structural and stereochemical complexity. Aspects of the methods include ring system distortion reactions that are systematically applied to rapidly convert readily available natural products to structurally complex compounds with diverse molecular architectures. Through evaluation of chemical properties including fraction of sp3 carbons, ClogP, and the number of stereogenic centers, these compounds are shown to be significantly more complex and diverse than those in standard screening collections. This approach is demonstrated with natural products (gibberellic acid, adrenosterone, and quinine) from three different structural classes, and methods are described for the application of this strategy to any suitable natural product.
A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products
Huigens III, Robert W.,Morrison, Karen C.,Hicklin, Robert W.,Flood J.r., Timothy A.,Richter, Michelle F.,Hergenrother, Paul J.
, p. 195 - 202 (2013/05/09)
High-throughput screening is the dominant method used to identify lead compounds in drug discovery. As such, the makeup of screening libraries largely dictates the biological targets that can be modulated and the therapeutics that can be developed. Unfortunately, most compound-screening collections consist principally of planar molecules with little structural or stereochemical complexity, compounds that do not offer the arrangement of chemical functionality necessary for the modulation of many drug targets. Here we describe a novel, general and facile strategy for the creation of diverse compounds with high structural and stereochemical complexity using readily available natural products as synthetic starting points. We show through the evaluation of chemical properties (which include fraction of sp 3 carbons, ClogP and the number of stereogenic centres) that these compounds are significantly more complex and diverse than those in standard screening collections, and we give guidelines for the application of this strategy to any suitable natural product.
Versatile Use of Hindered Oxalates for the Stereoselective Preparation of Novel 11-Modified Androst-5-ene Derivatives
Lecomte, Vincent,Stephan, Elie,Rager, Marie-Noelle,Jaouen, Gerard
, p. 3216 - 3219 (2007/10/03)
The 11α- and 11β-modified androst-5-ene derivatives 3a,b as well as the exo- and endocyclic dehydrated compounds 4a-c and 5b-c were produced using the oxalate derivatives of the highly hindered 11β-hydroxyandrost-5-enes 1a-c. The 11-tetrahydrofuran deriva
Improved addition of organolithium reagents to hindered and/or enolisable ketones
Lecomte, Vincent,Stéphan, Elie,Le Bideau, Franck,Jaouen, Gérard
, p. 2169 - 2176 (2007/10/03)
A study of the addition of some aryl- and alkyllithium derivatives to some hindered and/or enolisable ketones in different solvents (polar and apolar) and, in some cases, at different temperatures and reaction times, will be presented here. The reversibility of the addition of aryllithium to these specific ketones will be observed and discussed. This approach is then used to prepare new steroids as precursor for potentially interesting substituted testosterones.
