Asymmetric Synthesis of Drugs and Natural Products

Prof. Ahindra Nag is a Professor in the Chemistry Department at IIT Kharagpur. He has more than 3 decades of teaching and research experience. He has published 8 textbooks, 80 research papers in renowned journals and have guided 10 research scholars. He has also been granted with 3 industrial patents. He was invited as a Visting Professor in Academia Sinica (Taiwan), University of Molise ( Italy ) and Universty of Tennesse (USA).

• Chapter 1 Basic Stereochemical Approaches to Natural Products and Drugs.1.1Basic concept of Chirality.1.2 Meso compounds.1.3 Tautomerism and Valance Tautomerism. 1.4 Conformation.Fischer Projection and Absolute Configuration.1.5 Chiral Resolution. Application of Enantiomers in Drugs and Natural Products1.7. ReferencesProblems and answers Chapter- 2: Diastereoselective Addition of Organometallic Reagents to Chiral Carbonyl Compounds2.1. Introduction2.2. Models for Asymmetric carbonyl compounds addition2.3 Models for 1,3 Asymmetric carbonyl addition2.4. Addition reactions of achiral reagent2.5. Addition of aldehyde2.6. Addition of Chiral ketones2.7. Conclusion2.8. ReferencesChapter- 3: Enantiomerically Pure Compounds by Enantioselective Synthetic Chiral Metal Complexes3.1.Introduction3.2 History3.3. Mechanism of Dirhodium(II) – catalysed cycloprpanation reactions3.4.Electronic modifications4.1.2.Steric modifications3.5.Dirhodium ( II) carboxylate complexes3.6.Dirhodium(II) catalysts-derived from chiral N-protected amino acid ligands3.7.Dirhodium(II) catalysts derived from substituted cyclopropane carboxylate ligands3.8.Dirhodium (II) carboxamidates complexes3.9.Effects of axial ligands on Enantioselectivity 3.10. Conclusion 3.11. ReferencesChapter – 4: Chirality Organization of Peptide and -Conjugated Polyanilines4.1. Introduction4.2 Chirality Organization of Peptides4.2.1 Chirality Organization of Peptides by Using Organic Molecular Scaffold4.2.2 Chirality Organization of Peptides by Using Organometallic Molecular Scaffold4.3 Synthesis of Optically Active Polyanilines4.3.1 Polymerization of Anilines in the Presence of a Chiral Acid4.3.2 Doping of Emeraldine Bases with a Chiral Acid4.3.3 Introduction of Chiral Groups into Polyanilines4.4 Chiral Complexation of Emeraldine Bases with Chiral Complexes4.5 Application of Optically Active Polyanilines4.6. Conclusion4.7.ReferenceChapter -5: Diastereoselective Syntheses of Iminosugars5.0. Introduction5.1. Syntheses from the Chiral Pool5.2. Bio-catalyzed syntheses.5.3. Asymmetric Syntheses5.4. Conclusion and Future Directions5.5. ReferencesChaptere-6: The use of specific new artificial or semisynthetic bio-catalysts for synthesis of regio- and enantioselective compounds6.1. Introduction6.2. Regioselective preparation of monodeprotected esters 6.3. RefrencesChapter – 7: Bioactive Natural Products and Their Structure-Activity Relationships Studies7.1 Introduction7.2 Anti-Microbial Natural Products7.3 Glutathione S-Transferase Inhibitors7.4 Acetylcholinesterase Inhibitors7.5.-Glucosidase Inhibitors7.6 Anti-Renin Natural Products7.7. ReferencesChapter-8: Asymmetric Biocatalysis in Organic synthesis of Natural Products8.1.Introduction8.2.Prochirality. meso compounds8.3.The enzymatic desymmetrization8.4.Factors affecting an enzymatic reaction enantioselectivity8.5.Hydrolases8.6.Application of esterases and proteases in enzymatic desymmetrization of symmetrical compounds8.7.Application of lipases in enzymatic desymmetrization of symmetrical compounds8.8.Oxidoreductases 8.9. Application of dehydrogenases in enzymatic reduction of symmetrical compounds8.10. Application of ene-reductases in enzymatic reduction of symmetrical compounds8.11.Application of oxidases in enzymatic oxidation reactions of symmetrical compounds8.12.Application of peroxidases in enzymatic oxidation reactions of symmetrical compounds 8.13. ReferencesCHAPTER -9: Asymmetric Synthesis Of Biaryls And Axially Chiral Natural Products9.1. Introduction9.2.Chirality in biaryl compounds9.3.Bridged and nonbridged biaryl compounds9.4.Selective construction of biaryl axes9.5.Oxidative homocoupling in the presence of chiral additives9.6.Redox-neutral cross-coupling catalyzed by chiral metal complexes9.7.Transformations of stable but achiral biaryls and conformationally unstable but chiralbiaryls9.8.Desymmetrization of prostereogenicbiaryl compounds9.9.Conversion of axially chiral but conformationally unstable biaryl compounds - introduction of additional substituent in the ortho position9.10.Conversion of axially chiral but conformationally unstable biaryl compounds -bridge formation9.11.Conversion of axially chiral but conformationally unstable biaryl compounds -cleavage of a bridge9.12.Asymmetric axially chiral biarylsynthesis by construction of an aromatic ring9.13.ReferencesCHAPTER-10: Palladium-Catalyzed Asymmetric Transformations Of Natural Products And Drug Molecules10.1. Introduction10.2. Palladium-catalyzed asymmetric allylic alkylations10.3. Asymmetric Intramolecular cyclization reactions10.4. Palladium-catalyzed carbonylation reactions10.5. Conclusion and Future Perspectives10.6.ReferenceChapter-11: Enantioselective Organocatalysis from Concepts to Applications in the Synthesis of Natural Products and Pharmaceuticals11.1.Introduction11.2. Enamine Chemistry11.3.Modes of activation: iminium catalysis11.4.Cascade reactions based on iminium/enamine chemistry11.5 Application in total synthesis of organocascade reactions: Synthesis of Strychnine11.6.Conclusions11.7.ReferencesChapter-12: Chiral Building Blocks for Drugs Synthesis via Biotransformations12.1. Introduction12.2. Anticancer Drugs12.3 Small molecules12.4 Antidiabetic Drugs.12.5. Anti-inflammatory Drugs: Profens12.6. Drugs for treatment of Cardiovascular diseases12.7. Anticholesterol drugs12.8 Antihypertensive drugs12.8.1 β-BLOCKERS12.9 ACE inhibitors12.10 Calcium channel blockers12.11. Conclusion12.12.ReferencesChapter-13: Chiral Medicines13.1 Introduction13.2. Sitagliptin 13.3. Aprepitant 13.4. Simvastatin 13.5. Paroxetine 13.6. Levetiracetam 13.7 Pregabalin 13.8. Sertraline 13.9. Conclusions 13.10. References Chapter -14: Drug Delivery Systems14.1. Introduction14.2. Classification of drugs 14.3. Prodrug 14.4.Mode of action of drug14.5. Sites of Drug Action14.6.Goal of Drug delivery 14.7. Safety considerations14.8.Drug Distribution14.9.Further readingProblems to be solved