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T. L.S. Kishbaugh: Metalation of Pyrrole.- K.-S. Yeung: Furans and Benzofurans.- P. E. Alford: Lithiation-Based and Magnesation-Based Strategies for the Functionalization of Imidazole: 2001–2010.- L. Fu: Metalation of Oxazoles and Benzoxazoles.- S. Roy • S. Roy • G. W. Gribble: Metalation of Pyrazoles and Indazoles.- J. C. Badenock: Metalation Reactions of Isoxazoles and Benzisoxazoles.- Y.-J. Wu: Thiazoles and Benzothiazoles.- C. F. Nutaitis: Isothiazoles and Benzisothiazoles.- E. R. Biehl: Recent Advances in the Synthesis of Thiophenes and Benzothiophenes.- J. M. Lopchuk: Mesoionics.- J. M. Lopchuk: Azoles with 3-4 Heteroatoms.

Richard J. Sundberg Electrophilic Substitution Reactions of Indoles Tara L.S. Kishbaugh Reactions of Indole with Nucleophiles Erin Pelkey Metalation of Indole Jie Jack Li ∙ Gordon W. Gribble Metal-Catalyzed Cross-Coupling Reactions for Indoles Jeanese C. Badenock Radical Reactions of Indole Fariborz Firooznia ∙ Robert F. Kester ∙ Steven J. Berthel [2+2], [3+2] and [2+2+2] Cycloaddition Reactions of Indole Derivatives Robert F. Kester ∙ Steven J. Berthel ∙ Fariborz Firooznia [4+2] Cycloaddition Reactions of Indole Derivatives Jonathon S. Russel Oxindoles and Spirocyclic Variations: Strategies for C3 Functionalization Liangfeng Fu Advances in the Total Syntheses of Complex Indole Natural Products

Despite the long association of organohalogen compounds with human activities, nature is the producer of nearly 5,000 halogen-containing chemicals. Once dismissed as accidents of nature or isolation artifacts, organohalogen compounds represent an important and ever growing class of natural products, in many cases exhibiting exceptional biological activity. Since the last comprehensive review in 1996 (Vol. 68, this series), there have been discovered an additional 2,500 organochlorine, organobromine, and other organohalogen compounds. These natural organohalogens are biosynthesized by bacteria, fungi, lichen, plants, marine organisms of all types, insects, and higher animals including humans. These compounds are also formed abiogenically, as in volcanoes, forest fires, and other geothermal events.In some instances, natural organohalogens are precisely the same chemicals that man synthesizes for industrial use, and some of the quantities of these natural chemicals far exceed the quantities emitted by man.

This book summarizes the state-of-the-art knowledge on naturally occurring organohalogens, of which more than 3700 are documented. The chapters cover all aspects of this field, including the structural diversity and sources of organohalogens, the mechanisms for their formation and biodegradation, the clinical use of dichloroacetate, and the synthesis of the powerful anticancer chlorine-containing cryptophycin. Both biogenic and abiogenic sources of organohalogens are treated, the latter of which include volcanic emissions and abiogenic formation in soil. Halogenation in humans, fungi, and in the ocean are covered in separate chapters. Sources and biosynthesis of the relatively rare natural organofluorines are also discussed in this volume. By better understanding of the role nature plays in the area of organohalogens, we can more intelligently regulate the production, use, and disposal of man-made organohalogen compounds.