Stereoselective Synthesis of Drugs and Natural Products

Emphasizing synthetic strategy and practice, Stereoselective Synthesis of Drugs and Natural Products features experimental procedures for stereoselective synthetic reactions applicable to drug targets and natural products. Compiling material from leading contributors into one cohesive resource, this practical resource on synthetic methodology, reaction mechanisms, and applications for medicinal chemistry and drug discovery explores strategy and interdisciplinary work, laboratory synthesis for natural products, the preparative aspects of stereoselective synthesis for drugs, natural products, and potential biologically active compounds. The text also features experimental procedures for the different reaction methods covered. INDICE: Preface List of contributors List of symbols and abbreviations PART 1: GENERAL METHODS AND STRATEGIES Chapter 1: Principles, concepts and strategies of stereoselective synthesis Vasyl Andrushko and Natalia Andrushko Chapter 2: Chiral auxiliaries in drug synthesis Stanley Chang, Shira D. Halperin, Jarod Moore and Robert Britton Chapter 3: Solid–phase organic synthesis of drugs and natural products Peter J. H. Scott Chapter 4: Asymmetric phase–transfer catalysis Kohsuke Ohmatsu, Daisuke Uraguchi, and Takashi Ooi Chapter 5: Microwave–assisted stereoselective synthesis Yoann Coquerel, Evelina Colacino, Jean Rodriguez, Jean Martinez and Frédéric Lamaty Chapter 6: Application of micro reactor methodology for organic synthesis Paul Watts and Charlotte Wiles PART 2: STEREOSELECTIVE SYNTHESIS BY BOND FORMATION 2.1. STEREOSELECTIVE METHODS FOR C–C BOND FORMATION Chapter 7: Asymmetric α–alkylation of aldehydes, ketones and carboxylic acids Mark C. Kohler, Sarah E. Wengryniuk, and Don M. Coltart Chapter 8: Asymmetric aldol reactions in the total syntheses of natural products Seijiro Hosokawa Chapter 9: Asymmetric Michael addition and related reactions Pengfei Li, Jun Wang and Fuk Yee Kwong Chapter 10: Construction of polypropionate fragments in natural product synthesis Maris Turks, Sylvain Laclef and Pierre Vogel Chapter 11: Organocatalytic conjugate addition in stereoselective synthesis Adrien Quintard and Alexandre Alexakis Chapter 12: Stereoselective Nozaki–Hiyama–Kishi reaction Pat Guiry and Gráinne Hargaden Chapter 13: Transition–metal–catalyzed asymmetric C–C cross–couplings in stereoselective synthesis Vasiliki Sarli Chapter 14: Asymmetric hydroformylation, hydroxy– and alkoxycarbonylation for stereoselective synthesis Jamie T. Durrani and Matthew L. Clarke Chapter 15: Intramolecular oxycarbonylation in stereoselective synthesis Tibor Gracza Chapter 16: Stereoselective cycloaddition reactions Tae–Kyung Lee and Jung–Mo Ahn Chapter 17: Sigmatropic rearrangements in stereoselective synthesis Brinton Seashore–Ludlow and Peter Somfai Chapter 18: Ring contraction reactions in the total synthesis of biologically active natural products Luiz F. Silva Jr. Chapter 19: Electrocyclic reactions in stereoselective synthesis Marcus A. Tius Chapter 20: Transannular cyclization in natural product total synthesis Jiong Yang and Haoran Xue Chapter 21: Cascade reactions in stereoselective synthesis Bor–Cherng Hong and Nitin S. Dange Chapter 22: Sulfur dioxide: a powerful tool for the stereoselective construction of C–C bonds Pierre Vogel, Dean Markovic and Mâris Turks Chapter 23: Transition metal C–H activation: application to stereoselective synthesis of natural products and drugs Mickaël Jean and Pierre van de Weghe Chapter 24: Metathesis reactions in drug and natural product synthesis Akio Saito, Yuji Hanzawa Chapter 25: Radicals in stereoselective C–C bond formation Josep Bonjoch, Ben Bradshaw and Faïza Diaba Chapter 26: Trifluoromethyl (CF3) group insertion methods in stereoselective synthesis Tsutomu Konno Chapter 27: Stereoselective organocatalyzed C–C bond–forming reactions Kazuo Nagasawa and Koji Yasui Chapter 28: Enzyme–catalysed stereoselective C–C bond formation reactions in total syntheses Adeline Ranoux and Ulf Hanefeld 2.2. STEREOSELECTIVE METHODS FOR C–H BOND FORMATION Chapter 29: Stereoselective hydrogenation of C=C bonds: application to drug and natural product synthesis Natalia Andrushko and Vasyl Andrushko Chapter 30: Asymmetric hydrogenation of C=O and C=N bonds in stereoselective synthesis Natalia Andrushko and Vasyl Andrushko Chapter 31: Asymmetric protonation of carbanions and polar double bonds: application to total syntheses Thomas Poisson and Shu Kobayashi Chapter 32: Organocatalytic reduction in stereoselective synthesis Felix Kortmann and Adriaan Minnaard Chapter 33: Biocatalytic asymmetric reduction of C=O and activated C=C bonds in stereoselective synthesis Tomoko Matsuda, Rio Yamanaka and Kaoru Nakamura 2.3. STEREOSELECTIVE METHODS FOR C–O BOND FORMATION Chapter 34: Transition–metal–catalyzed stereoselective oxidations in drug and natural product synthesis Alessandro Scarso and Giorgio Strukul Chapter 35: Asymmetric epoxidation in stereoselective synthesis Zhicai Yang Chapter 36: Biocatalytic asymmetric oxidations in stereoselective synthesis Anett Schallmey, Pablo Dominguez de Maria and Paula Bracco Chapter 37: Ether transfer methodology: application to the synthesis of polyketide natural products Eric Stefan and Richard E. Taylor Chapter 38: Stereoselective formation of 2–deoxyglycosidic bonds in biologically active natural products Daisuke Takahashi and Kazunobu Toshima 2.4. STEREOSELECTIVE METHODS FOR C–N BOND FORMATION Chapter 39: Asymmetric hydroamination and reductive amination in total synthesis Manas K. Ghorai, Deo Prakash Tiwari and Aditya Bhattacharyya Chapter 40: Carboamination and alkylative cyclization with C–N bond formation in stereoselective syntheses Manas K. Ghorai, Sandipan Halder and Sauvik Samanta Chapter 41: Cycloadditions with stereoselective C–N bond formation in total syntheses Guillaume Vincent 2.5. STEREOSELECTIVE FORMATION OF OTHER C–HETEROATOM AND OTHER BONDS Chapter 42: Stereoselective halogenations Chong Kiat Tan, Yi Zhao, Jing Zhou and Ying–Yeung Yeung Chapter 43: Stereoselective synthesis of halogenated natural products Takehiko Yoshimitsu Chapter 44: Asymmetric fluorination methods: application in the stereoselective synthesis of fluorinated drugs Vincent Bizet and Dominique Cahard Chapter 45: Enzymatic halogenation in stereoselective synthesis Cormac D. Murphy and Benjamin R. Clark Chapter 46: Stereoselective carbon–sulfur (C–S) bond formation Kyungsoo Oh Chapter 47: Stereoselective methods for carbon–phosphorus (C–P) bond formation Marcin Kalek and Jacek Stawinski Chapter 48: Transition–metal–catalyzed asymmetric sulfoxidation in drug and natural product synthesis Alessandro Scarso and Giorgio Strukul PART 3: METHODS OF ANALYSIS AND CHIRAL SEPARATION Chapter 49: NMR–Spectroscopy in drug and natural product analysis Stanisuaw Witkowski and Iwona Wawer Chapter 50: Determination of enantiomeric purity and absolute configuration by NMR spectroscopy Thomas J. Wenzel Chapter 51: Solid–state NMR spectroscopy in drug design and discovery David A. Middleton and Simon G. Patching Chapter 52: Capillary electrophoresis in chiral separations Ans Hendrickx, Debby Mangelings and Yvan Vander Heyden Chapter 53: Determination of absolute configuration using chiroptical methods Joao Marcos Batista, Jr. Chapter 54: Chiral chromatographic methods in the analysis and purification of enantiomers Arnau Novell and Cristina Minguillón Chapter 55: X–Ray crystallography and 1H NMR anisotropy methods for determination of absolute configurations Nobuyuki Harada Chapter 56: Crystallization based separation of enantiomers Yaling Wang and Alex Chen Chapter 57: Enzymatic dynamic kinetic resolution in stereoselective synthesis Francisca Rebolledo, Javier González–Sabín, and Vicente Gotor Subject index

• ISBN: 978-1-118-03217-6
• Editorial: Wiley–Blackwell
• Encuadernacion: Rústica
• Páginas: 1852
• Fecha Publicación: 06/09/2013
• Nº Volúmenes: 2
• Idioma: Inglés