Synthetic Applications of Furan Diels-Alder Chemistry

Over the last two decades, electrophilic catalysis relying on platinum(II), gold(I), and gold(III) salts has emerged as a remarkable synthetic methodology. Chemists have discovered a large variety of organic transformations that convert a great assortment of highly functionalized precursors into valuable final products. In many cases, these methodologies offer unique features, allowing access to unprecedented molecular architectures. Due to the mild reaction conditions and high function compatibility, scientists have successfully developed applications in total synthesis of natural products, as well as in asymmetric catalysis. In addition, all these developments have been accompanied by the invention of well-tailored catalysts, so that a palette of different electrophilic agents is now commercially available or readily synthesized at the bench.In some respects, researchers’ interests in developing homogeneous gold catalysis can be compared with the Californian gold rush of the 19th century. It has attract...

Molecular complexity from polyunsaturated substrates: the gold catalysis approach.

In the past decade alkynes have become attractive starting materials for the synthesis of a variety of indole derivatives. This review summarizes the development of diverse homogeneous catalytic methods for the synthesis of indoles from alkynes and different N nucleophiles such as arylhydrazines, aniline derivatives, aryl isonitriles and nitroarenes.

Catalytic Synthesis of Indoles from Alkynes

Compounds and salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof and uses thereof are described. In certain aspects and embodiments, the described compounds or salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof are active on at least one Raf protein kinase. In certain aspects and embodiments, the described compounds are active in inhibiting proliferation of a Ras mutant cell line. Also described are methods of use thereof to treat diseases and conditions, including diseases and conditions associated with activity of B-Raf V600E mutant protein kinase, including melanoma, glioma, glioblastoma multiforme, pilocytic astrocytoma, colorectal cancer, thyroid cancer, lung cancer, ovarian cancer, prostate cancer, liver cancer, gallbladder cancer, gastrointestinal stromal tumors, biliary tract cancer, and cholangiocarcinoma. Also described are methods of use thereof to treat diseases and conditions, including diseases and conditions associated with activity of c-Raf-1 protein kinase, including acute pain, chronic pain or polycystic kidney disease.

Compounds and methods for kinase modulation, and indications therefor

Indoles are the most abundant heterocycles in biologically active natural products, pharmaceuticals, agrochemicals, and are relevant substructures in functional materials. As a result, the development of methodologies that enable the synthesis of these compounds is continuously demanded. This review summarizes most recent and relevant approaches towards the preparation of this prevalent structural motif.

Recent advances in indole syntheses: New routes for a classic target

From PtCl2‐ and Acid‐Catalyzed to Uncatalyzed Cycloisomerization of 2‐Propargyl Anilines: Access to Functionalized Indoles

p-Tolyl vinyl sulfoxide has been efficiently activated for Diels-Alder reactions by transformation into a sulfonium salt 3a or by addition of TMSOTf. Very high diastereomeric excesses have been achieved (>98%) at −20°C in many cases. Best results have been obtained with cyclopentadiene, furan and 2,3-dimethyl-1,3-butadiene. In this way enantiomerically pure oxanorbornenone 19a has been prepared. The reaction mechanism is briefly discussed.

Highly diastereoselective Diels-Alder reactions with (R)-ethoxy p-tolyl vinyl sulfonium tetrafluoroborate

The invention relates to specific novel 7-aza-indazoles having formula (I), which modulate the activity of proteins, particularly kinases, compositions containing same and the use thereof as a medicament, in particular as anticancer agents.

7-substituted aza-indazoles, compositions containing same, production method and use thereof

(R)-p-tolyl vinyl sulfoxide8 was transformed into the corresponding ethoxysulfonium compound9 which smoothly underwent reaction with 5-benzyloxymethyl-1,3-cyclopentadiene2 to give, after basic treatment, the bicyclic sulfoxide10 with very high de. This compound was transformed in three steps into enantiomerically pure norbornenone1, a key intermediate in some Corey syntheses of prostaglandins.

Highly enantioselective synthesis of a Corey prostaglandin intermediate

Isoindolone derivatives, preparation process and intermediates of this process, their use as medicaments, and pharmaceutical compositions comprising them. The present invention relates to the novel isoindolone derivatives of the Formula (I), in which R1 to R6 have the meanings stated in the claims. The inventive compounds are suitable as antiarrhythmic medicaments with a cardioprotective component for infarction prophylaxis and infarction treatment and for the treatment of angina pectoris. They also inhibit in a preventive manner the pathophysiological processes associated with the development of ischemia-induced damage, in particular in the triggering of ischemia-induced cardiac arrhythmias and of heart failure.

Baptiste Ronan

Papers

From PtCl2‐ and Acid‐Catalyzed to Uncatalyzed Cycloisomerization of 2‐Propargyl Anilines: Access to Functionalized Indoles

Highly diastereoselective Diels-Alder reactions with (R)-ethoxy p-tolyl vinyl sulfonium tetrafluoroborate

7-substituted aza-indazoles, compositions containing same, production method and use thereof

Highly enantioselective synthesis of a Corey prostaglandin intermediate

N- ((3-oxo2, 3-dihydro-1h-isoindol-1-yl) acetyl) guanidine derivatives as nhe-1 inhibitors for the treatment of infarction and angina pectoris