From Biosynthesis to Total Synthesis: Strategies and Tactics for Natural Products

Focusing on biosynthesis, this book provides readers with approaches and methodologies for modern organic synthesis. By discussing major biosynthetic pathways and their chemical reactions, transformations, and natural products applications; it links biosynthetic mechanisms and more efficient total synthesis.  Describes four major biosynthetic pathways (acetate, mevalonate, shikimic acid, and mixed pathways and alkaloids) and their related mechanisms  Covers reactions, tactics, and strategies for chemical transformations, linking biosynthetic processes and total synthesis  Includes strategies for optimal synthetic plans and introduces a modern molecular approach to natural product synthesis and applications  Acts as a key reference for industry and academic readers looking to advance knowledge in classical total synthesis, organic synthesis, and future directions in the field INDICE: 1. From Biosynthesis To Total Synthesis: An IntroductionBastien Nay and Xy–Wen Li .1.1 From Primary to Secondary Metabolism: the Key Building Blocks .1.1.1. Definitions .1.1.2. Energy supply and carbon storing at the early stage of metabolisms .1.1.3. Glucose as a starting material towards key building blocks of the secondary metabolism .1.1.4. Reactions involved in the construction of secondary metabolites .1.1.5. Secondary metabolisms .1.2 From Biosynthesis to Total Synthesis:Strategies towards the natural product chemical space .1.2.1. The chemical space of natural products .1.2.2. The biosynthetic pathways as an inspiration for synthetic challenges .1.2.3. The science of total synthesis .1.2.3. Conclusion: a journey in the future of total synthesis .1.3 Further reading on total synthesis and biosynthesis .ACETATE BIOSYNTHETIC PATHWAY .2. PolyketidesFransoiçe Schaefers, Tobias A. M. Gulder, Cyril Bressy, Michael Smietana, Erica Benedetti, Stellios Arseniyadis, Markus Kalesse, and Martin Cordes .2.1 Biosynthesis of polyketides .2.1.1. Introduction .2.1.2. Assembly of acetate/malonate derived metabolites .2.1.3. Classification of polyketide biosynthetic machineries .2.1.4. Conclusion .2.2 Synthesis of Polyketides .2.2.1. Asymmetric alkylation reactions .2.2.2. Application of asymmetric alkylation reactions in the total synthesis of polyketides and macrolides .2.3 Synthesis of polyketides focus on Macrolides .2.3.1. Introduction .2.3.2. Stereoselective synthesis of 1,3–diols–Asymmetric aldol reactions .2.3.3. Stereoselective synthesis of 1,3–diols–Asymmetric reductions .2.3.4. Application of stereoselective synthesis of 1,3–diols in the total synthesis of macrolides .2.3.4. Conclusion .3. Fatty AcidsAnders Vik and Trond Vidar Hansen .3.1 Introduction .3.2 Biosynthesis .3.2.1. Fatty acids and lipids .3.2.2. Polyunsaturated fatty acids .3.2.3. Mediated oxidations of –3 and –6 polyunsaturated fatty acids .3.3 Synthesis of –3 and –6 all–Z polyunsaturated fatty acids. .3.3.1. Synthesis of polyunsaturated fatty acids by the Wittig reaction or by the polyene semihydrogenation .3.3.2. Synthesis of polyunsaturated fatty acids via cross coupling reactions .3.4 Applications in total synthesis of polyunsaturated fatty acids .3.4.1. Palladium catalyzed cross–coupling reactions .3.4.2. Biomimetic transformations of polyunsaturated fatty acids .3.4.3. Landmark total syntheses .3.5 Conclusion .4. PolyethersYouwei Xie and Paul Floreancig .4.1 Introduction .4.2 Biosynthesis .4.2.1. Ionophore antibiotics .4.2.2. Marine ladder toxins .4.2.3. Annonaceous acetogenins and terpene polyethers .4.3 Epoxide reactivity and stereoselective synthesis .4.3.1. Regiocontrol in epoxide–opening reactions .4.3.2. Stereoselective epoxide synthesis .4.4 Application to total synthesis .4.4.1. Acid mediated transformations .4.4.2. Cascades via epoxonium ion formation .4.4.3. Cyclizations under basic conditions .4.4.4. Cyclization in water .4.5 Conclusion .MEVALONATE BIOSYNTHETIC PATHWAY .5. From Acetate to Mevalonate Biosynthetic PathwayAlexandros L. Zografos and Elissavet E. Anagnostaki .5.1 Introduction .5.2 Mevalonic acid pathway .5.3 Mevalonate–independent pathway .5.4 Conclusion .6. Monoterepenes and IridoidsMario Waser and Uwe Rinner .6.1 Introduction .6.2 Biosynthesis .6.2.1. Acyclic monoterpenes .6.2.2. Cyclic monoterpenes .6.2.3. Iridoids .6.2.4. Irregular monoterpenes .6.3 Asymmetric organocatalysis .6.3.1. Introduction and historical background .6.3.2. Enamine, Iminium and SOMO–activation .6.3.3. Chiral Bronsted acids and H–bonding donors .6.3.4. Chiral Bronsted/Lewis bases and nucleophilic catalysis .6.3.5. Asymmetric Phase Transfer Catalysis .6.4 Organocatalysis in the total synthesis of iridoids and monoterpenoid indole alkaloids .6.4 Conclusion .7. SesquiterpenesAlexandros L. Zografos and Elissavet E. Anagnostaki .7.1 Biosynthesis .7.2 Cycloisomerization reactions in organic synthesis .7.2.1 Enyne cycloisomerization .7.2.2 Diene cycloisomerization .7.3 Applications of cycloisomerizations in the total synthesis of sesquiterpenoids .7.3 Conclusion .8. DiterpenesLouis Barriault .8.1 Introduction .8.2 Biosynthesis of diterpenes based on cationic cyclizations, 1,2–shifts and transannular processes .8.3 Pericyclic reactions and their applications in the synthesis of selected diterpenoids .8.3.1 Diels–Alder reaction and its application in the total synthesis of diterpenes .8.3.2 Cascade pericyclic reactions and their application in the total synthesis of diterpenes .8.4 Conclusion .9. Higher Terpenes and SteroidsKazuaki Ishihara .9.1 Introduction .9.2 Biosynthesis .9.3 Cascade Polyene cyclizations .9.3.1 Distereoselective polyene cyclizations .9.3.2 Chiral proton–induced polyene cyclizations .9.3.3 Chiral metal ion–induced polyene cyclizations .9.3.4 Chiral halonium ion–induced polyene cyclizations .9.3.5 Chiral carbocation–induced polyene cyclizations .9.3.6 Stereoselective cyclizations of homo(polyprenyl)arene analogues .9.4 Biomimetic total synthesis of terpenes and steroids through polyolefin cyclization .9.5 Conclusion .SHIKIMIC ACID BIOSYNTHETIC PATHWAY .10. Lignans and LigninsYu Peng .10.1 Biosynthesis .10.1.1. Primary metabolism of shikimic acid and aromatic amino acids .10.1.2. Lignans and Lignin .10.2 Auxiliary assisted (sp3)–H arylation reactions in organic synthesis .10.3 Friedel–Crafts reactions in organic synthesis .10.4 Total synthesis of lignans by (sp3)–H coupling reactions .10.5 Total synthesis of lignans and polymeric resveratrol by Friedel–Crafts reactions .10.6 Conclusion .MIXED BIOSYNTHETIC PATHWAYS–THE STORY OF ALKALOIDS .11. Ornithine and Lysine AlkaloidsSebastian Brauch, Wouter S. Veldmate and Floris P. J. T.Rutjes .11.1 Biosynthesis of L–ornithine and l–lysine alkaloids1 .11.1.1. Biosynthetic formation of alkaloids derived from L–ornithine .11.1.2. Biosynthetic formation of alkaloids derived from L–lysine .11.2 The asymmetric Mannich reaction in organic synthesis .11.2.1. Chiral amines as catalysts in asymmetric Mannich reactions .11.2.2. Chiral Bronsted bases as catalysts in asymmetric Mannich reactions .11.2.3. Chiral Bronsted acids as catalysts in asymmetric Mannich reactions .11.2.4. Organometallic catalysts in asymmetric Mannich reactions .11.2.5. Biocatalytic asymmetric Mannich reactions .11.3 Mannich and related reactions in the total synthesis of L–lysine and L–ornithine derived alkaloids .11.4 Conclusion .12. Tyrosine AlkaloidsUwe Rinner And Mario Waser .12.1 Introduction .12.2 Biosynthesis of Tyrosine–derived alkaloids .12.2.1. Phenylethylamines .12.2.2. Simple tetrahydroisoquinoline alkaloids .12.2.3. Modified benzyltetrahydroisoquinoline alkaloids .12.2.4. Phenethylisoquinoline alkaloids .12.2.5. Amaryllidaceae alkaloids .12.2.6. Biosynthetic overview of tyrosine–derived alkaloids .12.3 Aryl–aryl coupling reactions .12.3.1. Copper–mediated aryl–aryl bond forming reaction .12.3.2. Nickel–mediated aryl–aryl bond forming reaction .12.3.3. Palladium–mediated aryl–aryl bond forming reaction .12.3.4. Transition metal couplings of non–activated aryl compounds .12.4 Synthesis of tyrosine–derived alkaloids .12.4.1. Synthesis of modified benzyltetrahydroisoquinoline alkaloids .12.4.2. Synthesis of phenylethylisoquinoline alkaloids .12.4.3. Synthesis of amaryllidaceae alkaloids .12.5 Conclusion .13. Histidine and Histidine–Like AlkaloidsIan S. Young .13.1 Introduction .13.2 Biosynthesis .13.3 Atom economy and Protecting–group free chemistry .13.4 Challenging the boundaries of synthesis. Pyrrole–imidazole alkaloids .13.5 Conclusion .14. Anthranilic Acid–Tryptophan AlkaloidsZhen–Yu Tang .14.1 Biosynthesis .14.2 Divergent synthesis–Collective total synthesis .14.3 Collective total synthesis of tryptophan–derived alkaloids .15. Future Directions of Modern Organic SynthesisJakob Pletz and Rolf Breinbauer .15.1 Introduction .15.2 Enzymes in Organic Synthesis–Merging Total Synthesis with Biosynthesis .15.3 Engineered Biosynthesis .15.4 Diversity oriented synthesis and biology oriented synthesis and diverted total synthesis .15.4.1. Diversity oriented synthesis .15.4.2. Biology oriented synthesis .15.4.3. Diverted total synthesis .Conclusion

• ISBN: 978-1-118-75173-2
• Editorial: Wiley–Blackwell
• Encuadernacion: Cartoné
• Páginas: 592
• Fecha Publicación: 11/05/2016
• Nº Volúmenes: 1
• Idioma: Inglés