Organic & Biomolecular Chemistry Blog

Alison R. Hardin Narayan and Richmond Sarpong have investigated the fundamental reactivity of indolizinones, relatively unexplored 6,5-N-fused bicycles.  They find that these bicycles have excellent ability to transfer stereochemistry  from the ring fusion position to other stereocenters, as well as readily undergoing Diels-Alder cycloadditions and selective hydrogenation, among other reactions.

To read more on the potential applications of indolizinones download the article now – it’s free to access for the next four weeks:

Indolizinones as synthetic scaffolds: fundamental reactivity and the relay of stereochemical information
Alison R. Hardin Narayan and Richmond Sarpong
DOI: 10.1039/C1OB06423A

Uncovering a new type of phosphoramidite prodrug, Piet Herdewijn et al. at the Katholieke Universiteit Leuven (Belgium) describe the synthesis and biological evaluation of phosphoramidate d4T derivatives against HIV. Some of the newly synthesized compounds were found to act as chain terminators for HIV-1 RT, thus inhibiting HIV-1 replication.

This article has been selected as HOT and will be FREE to access for a period of 4 weeks.
Read all about it here, and let us know what you think:

Synthesis and in vitro enzymatic and antiviral evaluation of phosphoramidate d4T derivatives as chain terminators Shiqiong Yang, Christophe Pannecouque, Eveline Lescrinier, Anne Giraut and Piet Herdewijn
DOI: 10.1039/C1OB06214J

This Hot Article by Christopher Frost et al. at the University of Bath (UK) describes the utility of novel silyl-protected dioxaborinanes, performing as excellent donors in rhodium-catalysed 1,4-addition reactions under anhydrous conditions. This approach allows the enantioselective addition to arylidene Meldrum’s acid derivatives and a subsequent asymmetric synthesis of 4-arylchroman-2-ones, an important class of bioactive and pharmaceutically-relevant compounds.

Why not read this OBC Communication now! It will be FREE to access for the next four weeks.

Rhodium-catalysed enantioselective synthesis of 4-arylchroman-2-ones
Joseph C. Allen, Gabriele Kociok-Köhn and Christopher G. Frost
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06586F, Communication

In this Hot Article, Alessandro Massi and colleagues at the University of Ferrara (Italy) disclose a novel approach to the Stetter reaction – the N-heterocyclic carbene (NHC)-catalyzed conjugate addition of acetyl anions to various α,β-unsaturated acceptors – in which 2,3-butandione (biacetyl) is used as an alternative surrogate of acetaldehyde.

We hope this new approach to NHC polarity reversal organocatalysis will catch your interest! You can read the article for FREE for the next 4 weeks.

Thiazolium-catalyzed intermolecular Stetter reaction of linear and cyclic alkyl α-diketones
Olga Bortolini, Giancarlo Fantin, Marco Fogagnolo, Pier Paolo Giovannini, Alessandro Massi and Salvatore Pacifico
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB06480K, Paper

The binding of two α-fucosylamide-based mimics of Lewis^X to DC-SIGN ECD (Dendritic Cell-Specific ICAM-3 Grabbing Nonintegrin extracellular domain) using STD NMR and docking studies has been investigated by Pedro M. Nieto and coworkers.  The mimics are shown to bind in a similar way to Lewis^X, through the fructose moiety and in a multi-modal fashion, but with increased affinity due to the aromatic moiety.

Insights into molecular recognition of Lewis^X mimics by DC-SIGN using NMR and molecular modelling
Cinzia Guzzi, Jesús Angulo, Fabio Doro, José J. Reina, Michel Thépaut, Franck Fieschi, Anna Bernardi, Javier Rojo and Pedro M. Nieto
Org. Biomol. Chem., 2011, 9, 7705-7712
DOI: 10.1039/C1OB05938F