The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.

Hcv ns3 protease inhibitors

The α-ketoamide motif is widely found in many natural products and drug candidates with relevant biological activities. Furthermore, α-ketoamides are attractive candidates to synthetic chemists due to the ability of the motif to access a wide range of functional group transformations, including multiple bond-forming processes. For these reasons, a vast array of synthetic procedures for the preparation of α-ketoamides have been developed over the past decades, and the search for expeditious and efficient protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged since the 1990s up to the present. The different synthetic routes have been grouped according to the way the α-ketoamide moiety has been created. Thus, syntheses of α-ketoamides proceeding via C(2)-oxidation of amide starting compounds are detailed, as are amidation approaches installing the α-ketoamide residue through C(1)-N bond formation. Also discussed are the methodologies centered on C(1)-C(2) σ-bond construction and C(2)-R/Ar bond-forming processes. Finally, the literature regarding the synthesis of α-ketoamide compounds by palladium-catalyzed double-carbonylative amination reactions is discussed.

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

Asymmetric aldol reactions of oxazolidinones as chiral auxiliaries have been achieved and attracted significant consideration as one of the most powerful synthetic tools for the carbon–carbon bond-forming reactions. The methodology has been highly successful in the stereoselective construction of a number of natural products, antibiotics, and other medicinally important compounds. The present review is focused on the utility and versatility of oxazolidinones (Evans chiral auxiliaries) in the asymmetric aldol condensations for the total synthesis of natural products and complex targets.

Oxazolidinones as chiral auxiliaries in asymmetric aldol reactions applied to total synthesis

Strategies and approaches for constructing 1-oxadecalins

Stereoselective Synthesis of β-(Hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones

Dibromomethane as one-carbon source in organic synthesis: a versatile methodology to prepare the cyclic and acyclic α-methylene or α-keto acid derivatives from the corresponding terminal alkenes

Dibromomethane as one-carbon source in organic synthesis: total synthesis of (±)- and (−)-methylenolactocin

The direct enantioselective construction of axially chiral 3-arylindole frameworks via nucleophilic addition of 2-substituted indoles to iminoquinones has been achieved with high efficiencies under mild chiral phosphoric acid (CPA) catalytic conditions. The utility of this method was demonstrated in successful scale-up syntheses without compromising the product yields and enantioselectivities. The oxidation of products yields axially chiral heteroaryl-p-quinone monoimine, which could be subjected to structural diversification via addition of nucleophiles.

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Enantioselective synthesis of 3-arylindole atropisomers via organocatalytic indolization of iminoquinones

Design, synthesis and anti-cancer evaluation of genistein-1,3,5-triazine derivatives

Ozonolysis of mono-substituted alkenes A-1 followed by reacting with a preheated mixture of CH2Br2–Et2NH affords α-substituted acroleins A-2 in good yields. Under very mild reaction conditions, these α-substituted acroleins A-2 can be easily converted to α-methylene esters A-4 , which could be further converted to the corresponding α-keto esters A-5 . This methodology can be also applied to the preparation of α-methylene lactones B-4 , α-methylene lactams, and α-keto lactones B-5 with various ring sizes.

Dibromomethane as One‐Carbon Source in Organic Synthesis: A Versatile Methodology to Prepare the Cyclic and Acyclic α‐Methylene or α‐Keto Acid Derivatives from the Corresponding Terminal Alkenes.

Yu-Wei Liu

Papers

Dibromomethane as one-carbon source in organic synthesis: a versatile methodology to prepare the cyclic and acyclic α-methylene or α-keto acid derivatives from the corresponding terminal alkenes

Dibromomethane as one-carbon source in organic synthesis: total synthesis of (±)- and (−)-methylenolactocin

Enantioselective synthesis of 3-arylindole atropisomers via organocatalytic indolization of iminoquinones

Design, synthesis and anti-cancer evaluation of genistein-1,3,5-triazine derivatives

Dibromomethane as One‐Carbon Source in Organic Synthesis: A Versatile Methodology to Prepare the Cyclic and Acyclic α‐Methylene or α‐Keto Acid Derivatives from the Corresponding Terminal Alkenes.