A Versatile Synthesis of Fluorinated Uracils in Solution and on Solid-Phase.

[reaction: see text] An efficient and convenient two-step synthesis of new fluorinated uracils is described. The first step involves the condensation of an ester enolate with a fluorinated nitrile to furnish fluorinated beta-enamino esters. In turn, these compounds react with organic isocyanates or isothiocyanates to give C-6 fluorinated uracils or thiouracils, respectively, in excellent yields. This synthesis has been successfully adapted to solid-phase conditions with high diversity, thereby facilitating the creation of small (thio)uracil libraries.

Synthetic and Biological Applications of Fluorous Reagents as Phase Tags

The search for new and better techniques for the purification of organic compounds has made the recent emergence of fluorous chemistry in the field of organic synthesis possible. Using fluorous reagents as phase tags allows for the access of different synthetic routes, and this has been translated into a time reduction and higher simplicity compared to standard, nonfluorous procedures. The synthesis in fluorous phase of target molecules can be pursued in a parallel or combinatorial manner in order to access chemical libraries with structural and/or stereochemical diversity. The preparation of radiolabeled molecules also benefits from the advantages of fluorous synthesis. Finally, biochemica…

Structure-Based Design of an RNA-Bindingp-Terphenylene Scaffold that Inhibits HIV-1 Rev Protein Function

Inside Back Cover: Structure-Based Design of an RNA-Bindingp-Terphenylene Scaffold that Inhibits HIV-1 Rev Protein Function (Angew. Chem. Int. Ed. 50/2013)

Enantioselective organocatalytic intramolecular aza-Michael reaction: a concise synthesis of (+)-sedamine., (+)-allosedamine, and (+)-coniine

The intramolecular aza-Michael reaction of carbamates bearing remote alpha,beta-unsaturated aldehydes under organocatalytic conditions took place with good yields and excellent ee's when Jorgensen catalyst IV was used in the process, giving rise to the enantioselective formation of several five- and six-membered heterocycles. The developed methodology was applied to the synthesis of three piperidine alkaloids.

Relay Catalysis: Enantioselective Synthesis of Cyclic Benzo-Fused Homoallylic Alcohols by Chiral BrOnsted Acid-Catalyzed Allylboration/Ring Closing Metathesis

Six- and seven-membered benzo-fused cyclic homoallylic alcohols can be readily synthesized by a tandem chiral BrOnsted acid-catalyzed allyl (crotyl)boration/ring closing metathesis sequence performed under orthogonal relay catalysis conditions. Excellent enantio- and diastereoselectivities are obtained in most of the cases. In addition, the parent crotylboration/RCM process is also described. The required substrates, ortho-vinylbenzaldehydes, are readily available in one step from commercially available starting materials. Both catalysts and reactants are also available from commercial suppliers. The reaction shows broad functional group compatibility and is also suitable for heteroaromatic…

Innenrücktitelbild: Structure-Based Design of an RNA-Bindingp-Terphenylene Scaffold that Inhibits HIV-1 Rev Protein Function (Angew. Chem. 50/2013)

CCDC 916244: Experimental Crystal Structure Determination

Related Article: Santos Fustero, Ignacio Ibáñez, Pablo Barrio, Miguel A. Maestro, Silvia Catalán|2013|Org.Lett.|15|832|doi:10.1021/ol3035142

CCDC 916245: Experimental Crystal Structure Determination

Related Article: Santos Fustero, Ignacio Ibáñez, Pablo Barrio, Miguel A. Maestro, Silvia Catalán|2013|Org.Lett.|15|832|doi:10.1021/ol3035142