Chemoselective oxidation of aromatic aldehydes to carboxylic acids: potassium tert-butoxide as an anomalous source of oxygen.

Chemoselective oxidation of aromatic and heteroaromatic aldehydes (>45 examples) to their corresponding carboxylic acids has been developed. Potassium tert-butoxide acts as an oxygen source during this transformation that delivers the corresponding acids without chromatographic purifications. The use of bench-top reagents, operational simplicity, and high level of chemo-selectivity with respect to oxidation of the least preferred aldehyde functionality, in the presence of more susceptible functional groups, are some of the highlights of this strategy.

HFIP-mediated C-3-alkylation of indoles and synthesis of indolo[2,3-b]quinolines & related natural products.

An expeditious metal free C-3 alkylation of indoles and its NIS-mediated deviation to indolo[2,3-b]quinolines is reported. This protocol, executed in aqueous HFIP has broad substrate scope and is well inclined towards the ideas of sustainable chemistry. Applications of these strategies in accessing bioactive natural products like vibrindole, norcryptotakeine, neocryptolepine and indenoindolone scaffolds has also been demonstrated.

A micelle-mediated approach enables facile access to bridged oxabicyclo[n.3.1]alkene scaffolds.

Oxabicyclo[n.3.1]alkene scaffolds present in a diverse range of complex natural products have been accessed by reacting 2-cycloalkenones with 1,3-cycloalkadiones in a micellar medium. This reaction occurring in a micellar confinement environment operates through a Michael addition/enolization/oxygen addition cascade to furnish highly functionalized constructs using a sustainable organic synthesis protocol. NMR analysis confirms that the locus of the solubilizates is within the palisade and stern regions of the micellar cavity.

Platanic Acid-Aryl Enones as Potential Anticancer Compounds: Synthesis and Biological Profiling against Breast, Prostate and Lung Cancer Cell Lines.

A series of rationally designed platanic acid-based compounds derived from naturally occurring betulinic acid were synthesized through a sequence of Lemieux-Johnson oxidation and Aldol condensation reaction. All the compounds were screened for cytotoxicity against a panel of human cancer and normal cell lines using MTT assay. From the biological data, it was observed that some of these semi-synthetic congeners exhibited potent biological profiles compared to platanic acid. One of the compounds with the p-tolyl substitution was found to be most active in this study, and its cytotoxicity against two of the cell lines, MDA-MB 231 and A-549 were in tune with the standard compound, 5-fluorouracil.