Anionic Annulations in Organic Synthesis

  • ID: 4519405
  • Book
  • 464 Pages
  • Elsevier Science and Technology
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Anionic Annulations in Organic Synthesis: A Versatile and Prolific Class of Ring-forming Reactions is a comprehensive review of the best annulations for the construction of cyclic structures and their applications in the total synthesis of functional molecules. 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 involved in many kinds of biologically active natural products and pharmaceutical drugs
  • Serves as a useful tool to academic and industrial researchers working on the synthesis of cyclic compounds as their targets
  • Includes many examples of anionic annulations and practical information on how to use them in research and industry
  • Features anionic annulations that are particularly useful for the synthesis of polyoxygenated polycyclic compounds, including tetracyclines, angucyclines, uncialamycins and lignans
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1. Annulations: history and perspectives
2. Hauser [4 + 2] annulation: Definition, history, mechanism, and types of phthalide donors and toluate donors
3. Lateral lithiations
4. [4+2] annulation of C3-nuclofugal phthalides (Hauser annulation) with
5. [4+2] annulation of non-activated phthalides (Sammes annulation) with
6. [4+2] annulation of homophthalic anhydrides (Tamura annulation) with
7. [4+2] annulation of activated o-toluate/o-tolualdehyde donors (Hauser-Leusen annulation)
8. [4+2] annulation with non-activated o-toluate donors (Staunton-Weinreb-Myers annulation)
9. Comparative chemistry of anionic [4+2] benzannulations of phthalides and toluates
10. Applications [4 + 2] anionic annulations in the total synthesis
11. Miscellaneous anionic annulations
12. Concluding remarks
Appendix: Problems and exercises
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Mal, Dipakranjan
Dipakranjan Mal began his studies at Calcutta University, where he received 1st class B.Sc.-Hons (1972) and M.Sc. (1975) degrees. He attended the University of Missouri at Kansas City for his Ph.D. degree in 1981 on intramolecular hydrogen bonding under Professor Layton L. McCoy. After a 3-year postdoctoral stint with Professor Frank M. Hauser at Oregon Graduate Center, he joined Bose Institute, Kolkata as a lecturer in 1984. Since 1987, he has been with the department of chemistry, Indian Institute of Technology Kharagpur, where he is now a higher administrative grade professor. His research interests are focused on the development of anionic and thermal domino strategies and total synthesis of angucyclines, anthracyclines, carbazoles, furocoumarins, and phthalide natural products. His notable discoveries are i) decarboxylative [4 + 2] annulation, ii) anionic [4 + 3] annulation and iii) an olefination based on thiophthalides. He has supervised 27 doctoral students and published over 120 research publications, including two reviews in Chemical Reviews. He has developed a 40-lecture video course on "Heterocyclic Chemistry” available on YouTube. He received the honor certificate of Phi Kappa Phi, U.S., in 1978. Recently, he was inducted as a Fellow of the West Bengal Academy of Science and Technology as well as Royal Society of Chemistry.
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