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Medicinal Natural Products: A Biosynthetic Approach. Third Edition. By Paul M. Dewick. John Wiley and Sons, Ltd., Chichester and Sussex, U.K. 2009. x þ 539 pp. 19 25 cm. ISBN978-0-470-74168-9. $170.00. This third edition of Medicinal Natural Products builds upon the biosynthetic approach to natural products presented in the previous two editions, with additional coverage of various genetic and molecular biological aspects of secondary metabolite biosynthesis. With the exception of only a few minor modifications, the general organization of the text is very similar to that of the previous versions. Seven years have passed since the publication of the second edition, and a considerable number of items has been updated, especially in regard to the books, reviews, and primary literature references recommended for further reading at the end of each chapter. The introduction (Chapter 1) entitled “About This Book and How To Use It” has been revised and includes more descriptive information under new subheadings such as “The Figures” with detailed guidelines for the use of the figures and schemes used in the book. Many of the figures throughout this edition have been significantly improved over those found in previous editions. Examples can be found from the very beginning of this volume, such as Figure 2.4 that details alkylation reactions, nucleophilic substitution, and Figures 2.7, 2.8, and 2.9 that depict aldol and Claisen reaction mechanisms. Some of the newly revised figures contain shorthand style “double-headed curly arrows” to represent addition-elimination mechanisms, which some students may find confusing. Many of these improved figures are clearer, as “R”-groups have replaced generic solid bars/ methyl groups as representations of generalized structural templates. Several reaction mechanisms have remained inaccurately represented or have been incorrectly depicted in a few of the revised figures. For example, the thermal decarboxylation reaction depicted for the gem-diacid in Figure 2.10 should involve the β-keto functionality and one of the carboxylic acid groups rather than act as a concerted reaction between the two carboxylic acid functionalities, as indicated. Similarly, the first step in phenolic oxidative coupling (Figure 2.27) requiring biological oxidants does not proceed via homolytic cleavage of the O-H bonds, as depicted. An acceptable mechanism would involve a one-electron oxidation of the hydroxy group that would yield an oxygen radical cation that would lose a proton to furnish the oxygen-centered radical. Chapter 2 contains an extremely brief new halogenation reaction subsection and a valuable subchapter on elucidating biosynthetic pathways. The latter provides an overview of traditional biosynthetic labeling studies and includes a discussion of modern genetic approaches to investigate the biogenetic origins of natural products. Considerable recent progress into the genetic and enzymatic processes involved in microbial polyketide synthases is represented by significantly updated sections on the biosynthesis of macrolide antibiotics, epothilones, and several other classes of natural products. The coverage of nonribosomal peptide biosynthesis (Chapter 7) has been significantly expanded and includes new figures related to the biosynthesis of aminosugars and aminoglycosides.
As in previous editions, the third edition uses highly informative “boxed” topics that provide additional accounts of medicinal natural products and related pharmaceuticals. These too have been updated to include new investigational agents and recently approved drugs. The overall focus of this edition continues to be plant natural products and, to a lesser extent, microbial metabolites. Each successive edition has incorporated a limited number of toxins and other marine compounds. Workers in the field of marine natural products chemistry and/or biosynthesis are likely to find this text to be generally useful but not very directly applicable to some unique aspects of marine natural products. This edition includes a significant quantity of additional new material without greatly increasing the number of pages and subsequent cost. In order to accomplish this, the text size has been reduced and typeset is in 9pt/11pt Times Roman that some may find more difficult to read. This new edition is an excellent text that is unrivaled in both its scope and overall coverage of natural products biosynthesis. While this book is designed for pharmacy students in the U.K., the biosynthesis of natural products is unlikely to exist in the typical U.S. pharmacy school curriculum. However, as a reference, mechanistic details covered in this text provide valuable insights for specific sections of undergraduate pharmacy courses in antibiotics and medicinal chemistry. The chemistry and biosynthesis of natural products continue to play an important component of many U.S. graduate programs. In this regard, we have found this text to be an invaluable resource and have adopted it as a primary text for our newly designed required graduate courses in natural products chemistry. Like the previous edition, an affordable paperback version is also available (ISBN 978-0-470-74167-2, $70.00). We believe Dewick’s third edition to be one of the most authoritative and useful texts of its kind. It skillfully combines aspects of natural products chemistry, biosynthesis, and clinically related pharmacology in an extremely useful book that can serve as either a course text or general reference. Jordan K. Zjawiony, Daneel Ferreira, and Dale G. Nagle* Department of Pharmacognosy and Research Institute of Pharmaceutical Sciences School of Pharmacy University of Mississippi University, Mississippi 38677
DOI: 10.1021/jm901204h Published on Web 08/28/2009
Organic Synthesis: The Disconnection Approach. Second Edition. By Stuart Warren and Paul Wyatt. Wiley, Hoboken, NJ. 2009. viii þ 329 pp. 19.5 25 cm. ISBN 0470712376. $140.00. This volume is an update of the first edition, published in 1982. As with the first edition, an accompanying workbook is planned. The organization of this second edition is highly similar to the first edition, and all 40 chapters are congruent with the original 40 chapters. Although strategy and topical chapters are interspersed, the overall outline is as
Book Reviews
follows: Chapters 1-7, a general description of the disconnection approach; Chapters 8-10, disconnections involving sp3 functional groups (amines and alcohols); Chapters 13-28, carbonyl and carbanion chemistry; Chapters 29-37 and Chapter 39, carbocyclic and heterocyclic ring synthesis; Chapters 12 and 38 stereochemistry; Chapter 40, advanced strategies. Overall, the content, focus, and enjoyable reading nature of the first edition are retained and expanded upon in the present edition. Modern synthetic topics such as atom efficiency and green chemistry, although not mentioned explicitly, are well represented throughout the book. A significant modification for the second edition is the presentation of references to reviews and primary articles at the end of each chapter; such references usually number fewer than 12. Each chapter also has a “Background Needed for this Chapter” section that references standard organic chemistry texts or monographs. Chapters 1-7 retain the focus of the first edition, with ample space devoted to aromatic addition and substitution reactions. New and additional emphasis is placed on the synthesis of drug substances. Chapters 8-10 are expanded and include a well-presented discussion of reductive alkylations in Chapter 8 and an expanded presentation of silyl protecting groups in Chapter 9. Chapters 13-28 continue the emphasis on updating terminology and presenting examples of synthesis of drug substances. Additions include an expanded Wittig reaction section (Chapter 15), a fuller elaboration of conjugated enolate systems (Chapter 20), an expanded nitro aldol section (Chapter 22), and a significantly updated section on 1, 4-difunctionalized compounds (Chapter 25). Chapters 27-29 and Chapter 39 again continue the emphasis of drug substances. There is included a good description of metal carbene reagents (Chapter 30), the role of ketenes in synthesis (Chapter 33), and a more lucid presentation of [3,3]-sigmatrophic shifts. Chapter 39, aromatic heterocycles, has been considerably shortened in the second edition. The stereochemistry chapters and the advanced strategies chapter (Chapters 12, 38, and 40) have undergone the most modification. Chapter 12 updates the stereochemical description nomenclature. Chapter 38 presents a greater emphasis on 1,2-fused bicyclic systems. Chapter 40 retains the analytical presentation of lycorane but presents it in the context of a “key reaction strategy”. Overall, the authors have succeeded admirably in the updating of a classic in the pedagogy of organic chemistry. Updates are, in general, appropriate. Representative of these changes is the selected applications of the Diels-Alder cyclization: Buchi’s cyclohexane study (1970) has been replaced by Nicolau’s synthesis of colombiasin A (2001) and Sorensen’s synthesis of a key intermediate for quanacastepenes (2002). This second edition nobly updates the first edition with a balance of classic syntheses, modern updates, and practical thinking in chemical efficiency. The book should be required reading for all synthetic medicinal chemistry graduate students and for first year graduate organic chemistry students who are contemplating a career in the pharmaceutical industry. It should be equally useful on the active reading shelves
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of practicing organic medicinal chemists in industry and academia. Patrick T. Flaherty Mylan School of Pharmacy Duquesne University 445 Mellon Hall Pittsburgh, Pennsylvania 15282
DOI: 10.1021/jm901038v Published on Web 08/25/2009
Organic Reactions. Volume 73. Edited by S. E. Denmark. John Wiley and Sons, New York. 2009. vii þ 607 pp. 16 24 cm. ISBN 0470436905. $140.00. The latest volume of the venerable Organic Reactions series represents a rare single chapter volume on allylboronation of carbonyl compounds. This privilege is reserved for extremely important chemical reactions. Allylboronation of carbonyl compounds has become a widely used method for the asymmetric formation of carbon-carbon bonds and is particularly well suited for the enantioselective synthesis of polyketide derived natural products. The chapter follows the standard Organic Reactions format covering the practical aspects relating to the use of this chemistry, including stability and handling of reagents, reactivity and workup details, mechanism and stereochemistry, scope and limitations, enantioselective synthesis, and application to natural product synthesis. Experimental details are provided for the preparation of commonly used starting materials and representative allyl boronation reactions of carbonyl compounds including some of those most widely used in enantioselective synthesis. The chapter concludes with a comprehensive 400-page tabular survey of this chemistry in the literature, covering over 800 citations. Although the tabular section is well organized, because of its sheer size, a minor concern is that it may be more expeditious to obtain reference data via alternative electronic database searching rather than leafing through this text. In summary, this well written volume of Organic Reactions makes an excellent library resource that comprehensively covers the chemistry of allylboronation of carbonyl compounds. It should make an excellent reference text for graduate students and researchers who are new to this reaction or for researchers who need inspiration for the use of this chemistry. This volume will also be a very useful personal reference text to those who specialize in this area of chemistry. Richard E. Lee Department of Pharmaceutical Sciences College of Pharmacy University of Tennessee Health Science Center Memphis, Tennessee 38163
DOI: 10.1021/jm900911u Published on Web 06/25/2009
