Bharatam Jagadeesh

A Flexible Enantioselective Total Synthesis of Diospongins A and B and Their Enantiomers Using Catalytic Hetero-Diels-Alder/Rh-Catalyzed 1,4-Addition and Asymmetric Transfer Hydrogenation Reactions as Key Steps

A unified enantioselective route to total synthesis of diospongins A and B and their enantiomers has been developed employing achiral starting materials. All three stereocenters were introduced by means of catalytic reactions.

β-Sugar aminoxy peptides as rigid secondary structural scaffolds

Short homo-oligomers of a new building block, cis-beta(2,3)-furanoid sugar aminoxy acid, are designed, characterized, and found to exhibit rigid ribbon-like secondary structures composed of 5/7 bifurcated intramolecular hydrogen bonds.

A Synthetic Zipper Peptide Motif Orchestrated via Co-operative Interplay of Hydrogen Bonding, Aromatic Stacking, and Backbone Chirality

Here, we report on a new class of synthetic zipper peptide which assumes its three-dimensional zipper-like structure via a co-operative interplay of hydrogen bonding, aromatic stacking, and backbone chirality. Structural studies carried out in both solid- and solution-state confirmed the zipper-like structural architecture assumed by the synthetic peptide which makes use of unusually remote inter-residual hydrogen-bonding and aromatic stacking interactions to attain its shape. The effect of chirality modulation and the extent of noncovalent forces in the structure stabilization have also been comprehensively explored via single-crystal X-ray diffraction and solution-state NMR studies. The results highlight the utility of noncovalent forces in engineering complex synthetic molecules with intriguing structural architectures.