Shantanu Pal

Synthesis and Antitumor Activity of Fluorocyclopentenyl-Pyrimidines

Synthesis of fluorocyclopentenyl pyrimidine nucleosides 6–9 was enantiopurely accomplished employing oxidative rearrangement, RCM reaction and electrophilic fluorination starting from d-ribose. Cytosine analog 8 was found to exhibit significant anticancer activity in various human tumor cell lines.

Highly regio- and diastereoselective, acidic clay supported intramolecular nitrile oxide-alkene cycloaddition on D-ribose derived nitriles: an efficient synthetic route to isoxazoline fused five and six membered carbocycles.

An efficient synthetic route to isoxazoline fused carbocycles from carbohydrate scaffolds that comprise of free hydroxyl group(s) is described with high regio- and stereoselectivity. Montmorillonite K-10/chloramine T oxidation and in situ intramolecular nitrile oxide-alkene cycloaddition (INOC) of D-ribose derived oximes have been developed for the diversity oriented synthesis of isoxazoline fused five and six membered carbocycles.

Lead tetraacetate mediated one pot oxidative cleavage and acetylation reaction: an approach to apio and homologated apio pyrimidine nucleosides and their anticancer activity

An efficient and versatile strategy of general applicability towards apio and homologated apio pyrimidines has been delineated. The methodology shows tosylation followed by in situ cyclization and one pot oxidative cleavage and acetylation by Pb(OAc)4 as the key steps. The methodology has been applied to D-ribose and D-mannose derivatives to achieve asymmetric synthesis of apio and homologated apio pyrimidine nucleosides.

Cycloaddition of cyclohexa-2,4-dienones with electron deficient 2π partners: a novel and stereoselective route to functionalised bicyclo[2.2.2]octenones

A novel route to functionalised bicyclo[2.2.2]octenones via pi 4s + pi 2s cycloaddition of cyclohexa-2,4-dienones with electron deficient 2 pi partners, and crystal structure of 1,7-dimethyl-5-hydroxy-5-chloromethyl-2-carboethoxy bicyclo[2.2.2]oct-7-ene-6-one, is reported.

A common and versatile synthetic route to (-) and (+) pentenomycin I, (+) halopentenomycin I and dehydropentenomycin.

A versatile and stereoselective total synthesis of (+) and (-) pentenomycin I, (+) halopentenomycins I and dehydropentenomycin from a common chiral polyhydroxylated cyclopentene through oxidation and protection/deprotection has been described. Stereoselective hydroxymethylation, stereoselective Grignard reaction and ring closing metathesis are the key features of our approach.

Stereoselective Synthesis Of Homo-Apioneplanocin A As Potential Inhibitor Of S-Adenosylhomocysteine Hydrolase

Homo-apioneplanocin A (1) as a potential inhibitor of S-adenosylhomocysteine hydrolase was synthesized from D-ribose, employing stereoselective hydroxymethylation, regioselective oxidation, and regio- and chemoselective hydroboration as key steps.

Novel homologated-apio adenosine derivatives as A3 adenosine receptor agonists: design, synthesis and molecular docking studies

Synthesis of a series of novel homologated-apio adenosine analogues including homologated-apio IB-MECA and Cl-IB-MECA has been accomplished from a commercially available, inexpensive starting material D-ribose. The synthetic route includes a controlled oxidative cleavage of vicinal diol and Mitsunobu condensation reactions as the key steps. The molecular docking studies of the synthesized compounds to the A3 adenosine receptor model indicated them as agonists. Interestingly, some of the molecules showed good binding interactions at the active site as evident by docking scores and MM/GBSA binding affinity.