Spiro Compounds. Группа авторов
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14 9 Transition‐Metal‐Catalyzed Dearomative Spiroannulation Reactions 9.1 Introduction: Discovery of Aromatic Compounds 9.2 Development of Dearomatization Reactions 9.3 Development of Dearomative Spiroannulation Reactions 9.4 Dearomative Spiroannulations of Phenols 9.5 Dearomative Spiroannulation of Indoles 9.6 Dearomative Spiroannulation of Aromatic Heterocyclic Compounds 9.7 Dearomative of Other Aromatic Compounds 9.8 Conclusion References
15 10 Carbocyclic Spiro Compounds Occupying Higher Dimensions: Benzoannelated [5.5.5.5]Fenestranes and Beyond 10.1 Introduction 10.2 Selected Synthesis Strategies 10.3 Conclusions Acknowledgements References
16 11 The Synthesis of Natural Products Containing Spirocycles 11.1 Porco’s Synthesis of (+)‐Calafianin [2] 11.2 Hayashi’s Total Synthesis of Pseurotin A[6] 11.3 Trost’s Synthesis of (−)‐Ushikulide A [12] 11.4 Castle’s and Herzon’s Syntheses of (−)Acutumine 11.5 Overman’s and Carreira’s Synthesis of Spirotryprostatin B 11.6 Conclusion References
17 Index
List of Tables
1 Chapter 2Table 2.1 Selected examples of FDA‐ approved drugs containing spirocyclic m...Table 2.2 Physicochemical and biochemical properties of selected oxetanes, ...Table 2.3 Comparison of the properties of spirocyclic oxetanes with their m...
List of Illustrations
1 Chapter 1Figure 1.1 Growing interest in spiro compounds in chemical literature.Figure 1.2 Dye sensitizer 9,9‐spirobifluorene.Figure 1.3 Donor–acceptor spiro compounds and colors displayed by them.Figure 1.4 Examples of naturally occurring compounds containing the spiro mo...Figure 1.5 Spiro functionality in nicotinic receptor antagonists.Figure 1.6 Examples of marketed spiro compound drugs.Figure 1.7 ACC inhibitors of pharmaceutical interest.Figure 1.8 Commercial spirocyclic insecticide/acaricide products.Figure 1.9 Recently patented spiro compound of agrochemical interest.Figure 1.10 Example of numbering of spirocyclic compounds.Figure 1.11 Example of naming chiral spiro compounds.
2 Chapter 2Figure 2.1 X‐ray crystal structure (pdb 2gfx12) of Platensimycin (2, sticks ...Scheme 2.1 Key enyne cycloisomerization step in Nicolaou’s total synthesis o...Figure 2.2 Schematic comparison of substituted biaryl and spiro[3,4]octane s...Figure 2.3 Examples of saturated spirocyclic ring systems frequently encount...Figure 2.4 Examples of lead optimization employing spirocycles.Scheme 2.2 Summary of common strategies for the synthesis of common four‐mem...Figure 2.5 Comparison between carbonyl, gem‐dimethyl, and oxetane groups, hi...Figure 2.6 (a) Spiro‐oxetane as a morpholine bioisostere. (b) comparison...Figure 2.7 Replacement of morpholine by 2‐oxa‐6‐azaspiro[3.3]heptane in BTK ...Figure 2.8 Top: Structure of thalidomide 34 and its oxetano analogue 35. Bot...Figure 2.9 Representative examples of spirocyclic bioactive lead molecules....Figure 2.10 Additional examples further illustrating the breadth of ring typ...Figure 2.11 Representative examples of (a) multifunctional spiro building bl...
3 Chapter 3Scheme 3.1 Scandium‐catalyzed enantioselective carboannulation between alkyl...Scheme 3.2 Copper‐catalyzed asymmetric [3+2] cycloaddition between alkyliden...Scheme 3.3 Copper‐catalyzed asymmetric construction of dispiropyrrolidine sk...Scheme 3.4 Magnesium‐catalyzed asymmetric [3+2] cycloaddition between methyl...Scheme 3.5 Rhodium‐catalyzed enantioselective [3+2] annulation to form spiro...Scheme