Mahesh Reddy Ghanta

Novel Carbon–Carbon Bond Formation between N‐Methyl‐3‐phenyl‐3‐hydroxypropylamine and Cresols Catalyzed by p‐Toluenesulphonic Acid

Abstract The p‐toluenesulphonic acid–catalyzed reaction between appropriate cresols and N‐methyl‐3‐phenyl‐3‐hydroxypropylamine in refluxing toluene resulted in the formation of o‐substituted phenol derivatives by an aromatic nucleophilic substitution reaction.

Unexpected Synthesis of Highly Substituted Indole Derivatives

An unexpected synthesis of highly substituted indole derivatives was provided by treating 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-pentanoic acid phenylamide with aryl hydrazines in the presence of trifluoroacetic acid in tetrahydrofuran.

New Synthesis of Simvastatin

Abstract A noninfringing synthesis of simvastatin 1, starting from lovastatin 2, is presented. This synthesis features the protection of the free hydroxyl group of the lovastatin with 3,4-dihydro-2H-pyran (DHP) and opening of the lactone ring with n-BuNH2 to afford amide 4 as a key intermediate.

Unusual p-toluene sulfonic acid-catalyzed carbon-carbon bond formation

Abstract Attempts to synthesize the antidepressant drug atomoxetine directly by p-TSA‐catalyzed reaction between o‐cresol and N‐methyl‐3‐phenyl‐3‐hydroxypropyl amine in toluene at reflux temperature surprisingly resulted in the formation of ortho‐substituted phenol derivative. The structure is unambiguously confirmed by single crystal X-ray.