Anionic Annulations in Organic Synthesis: A Versatile and Prolific Class of Ring-Forming Reactions

Anionic Annulations in Organic Synthesis is a comprehensive review of the best annulations for construction of cyclic structures and their applications in the total synthesis and the synthesis of functional molecules. The annulation, another name for the ring formation with two new bonds of the ring, is a powerful tool in general organic synthesis as well as total synthesis of natural products.

The reactions described in the work are particularly useful for the synthesis of polyoxygenated polycyclic compounds, including tetracyclines, angucyclines, uncialamycins, and lignans, among other compounds. Included in detail are the Hauser, Robinson, Sammes and Meyers annulations, all of which can be effectively used to construct substrates with complex molecular structures. This work provides the tools to master anionic organic chemistry, ortho-lithiation, lateral lithaition/metalation and organic selectivity issues like chemoselectivity, regioselectivity and stereoselectivity.

This book is a valuable resource for organic chemists, researchers and students seeking a complete and detailed understanding of anionic annulations.

Provides a comprehensive review of anionic cyclization for chemical construction of a variety of cyclic scaffolds, which are involved in many kinds of biologically active natural products and pharmaceutical drugsServes as a useful tool to academic and industrial researchers working on synthesis of cyclic compounds as their targets, helping them identify the most efficient synthetic pathIncludes many actual examples of anionic annulations and practical information on how to use them in research and industryFeatures anionic annulations that are particularly useful for the synthesis of polyoxygenated polycyclic compounds, including tetracyclines, angucyclines, uncialamycins, and lignans

1. Introduction 2. Hauser [4 + 2] Annulation: Definition, History, Mechanism, and Types of Phthalide Donors and Toluate Donors 3. Lateral Lithiations 4. [4+2] Annulation of  3-Nuclofugal Phthalides (Hauser Annulation) 5. [4+2] Annulation With Nonactivated Phthalides  (Sammes Annulation) 6. [4+2] Annulation of Homophthalic Anhydrides 7. [4+2] Annulation of Activated o-Toluate/o-Tolualdehyde Donors (Hauser-Leusen Annulation) 8. [4+2] Annulation With Nonactivated o-Toluate Donors (Staunton-Weinreb-Myers Annulation) 9. Comparative Annulation Chemistry of Phthalides, Homophthalic Anhydrides and o-Toluates 10. Applications of [4+2] Anionic Annulations in the Total Synthesis 11. Miscellaneous Anionic Annulations 12. Concluding remarks Appendix: Problems and exercises