This long-awaited graduate level textbook adopts a refreshingly unique approach, and is written by one of the world's leading organic chemists. Following an introductory look at the concept of synthesis, the text goes on to discuss sources of enantiomerically pure compounds, the Chiron approach, locating the various substructures, synthesis with the various precursors and computer-aided synthesis. The whole is rounded off by an appendix with selected transformations of amino acids, carbohydrates, hydroxyacids and terpenes. A must-have source of first-class information for everyone working in organic synthesis, not only for graduate students.
Stephen Hanessian holds the Isis Pharmaceutical Research Chair at the University of Montreal and is also on the faculty of the Departments of Chemistry, Pharmaceutical Sciences and Pharmacology at the University of California, Irvine. He has received numerous awards and distinctions, the latest being the 2012 Ernest Guenther Award in the Chemistry of Natural Products from the American Chemical Society, and the IUPAC-Prize in Medicinal Chemistry.
Simon Giroux was born and raised in Montreal, Canada. He received his PhD in 2006 with Prof. Stephen Hanessian and subsequently spent 2 years in the laboratory of Prof. E. J. Corey at Harvard University, as an NSERC postdoctoral fellow. He is currently working as a medicinal chemist at Vertex Pharmaceuticals in Cambridge, Massachusetts.
Bradley L. Merner is a native of St. John?s, Newfoundland, Canada. He completed is PhD degree under the direction of Prof. Graham J. Bodwell at Memorial University working in the area of nonplanar aromatic hydrocarbon synthesis. In January of 2009, he moved to his current position as postdoctoral research associate in the laboratories of Prof. Stephen Hanessian at the University of Montreal.
Table of Contents
THE CONCEPT OF SYNTHESIS Organic Synthesis as a Central Science Organic Chemistry and the Public The "Small Molecules" of Life Nature's Rules Organic Synthesis as a Mental and Visual Science Art, Architecture, and Synthesis Simplification of Complexity Seeing Through the Mind?s Eye Beauty is in the Eye of the Beholder THE "WHY" OF SYNTHESIS Nature the Provider, Healer and Enticer The Supply Problem From Bench to Market Thank You Nature! Chasing Bugs with a Purpose Structure-Based Organic Synthesis Almost There The Futility of it All Synthesis as a Seeker of Truth Nature as the Ultimate Synthesizer A Brave New Chemical World Exploring New Synthetic Methods THE "WHAT" OF ORGANIC SYNTHESIS Periods, Trends, and Incentives A Century of Synthesis We the "Synthetic" People Complex and Therapeutic too! Peptidomimetics and Unnatural Compounds Diversity Through Complexity THE "HOW" OF SYNTHESIS The Visual Dialogue The Psychobiology of Synthesis Planning The Agony and Ecstasy of Synthesis Rembrandt Meets Woodward The Post Woodwardian Era Catalysis and Chirality in Total Synthesis SOURCES OF ENANTIOPURE COMPOUNDS Optical Resolution Chemical Kinetic Resolution (KR) Cell-Free Enzyme-Mediated Enantiopure Compounds Cell-Free Chemoenzymatic Methods Metal-Catalyzed Dynamic Chemical Resolution (DCR) Biocatalytic Methods for Enantiopure Compounds Applications of Enzymatic and Chemoenzymatic Methods Chemical Asymmetric Synthesis of Enantiopure Compounds Enantiopure Compounds from Nature THE CHIRON APPROACH Living Through a Total Synthesis Principles of the Chiron Approach Anatomy of a Synthesis NATURE'S CHIRONS Alpha-Amino Acids Carbohydrates Alpha-Hydroxy Acids Terpenes Cyclitols FROM TARGET MOLECULE TO CHIRON Where's Waldo? Apparent Chirons Partially Hidden Chirons Hidden Chirons Chirons as "Sacrificial Lambs" Locating Amino Acid-Type Substructures Locating Carbohydrate-Type Substructures Locating Hydroxy Acid-Type Substructures Locating Terpene-Type Substructures Locating Carbocyclic-Type Substructures Locating Chirons Derived from Lactones APPLICATIONS OF THE CHIRON APPROACH Category I Target Molecules Category II Target Molecules Category III Target Molecules Prelude to Total Synthesis of Category I Molecules TOTAL SYNTHESIS FROM AMINO ACID PRECURSORS Actinobolin Aspochalasin B Cephalotaxine Alpha-Kainic Acid Alpha-Kainic Acid Croomine Biotin Salinosporamide A Thienamycin FR901483 Tuberstemonine Phyllanthine Oscillarin Miscellenea TOTAL SYNTHESIS FROM CARBOHYDRATE PRECURSORS Ajmalicine Actinobolin trehazolin and Trehazolamine Fomannosin 9Alpha-Desmethoxy Mitomycin A Saxitoxin Decarbamoyl ent. Saxitoxin Zaragozic Acid A Hemibrevitoxin B Carbohydrates in Synthesis and Biology Miscellanea TOTAL SYNTHESIS FROM HYDROXY ACIDS Griseoviridin Halicholactone Brasilenyne Octalactin A (3Z)-Dactomelyne UCS 1025A Miscellanea TOTAL SYNTHESIS FROM TERPENES Picrotoxinin Eucannabinolide Trilobolide and Thapsivillosin Briarellin E and F Samanderine Y Ambiguine H and Hapalindole U Platensimycin Phomactin A Pinnaic Acid Fusicoauritone Miscellanea TOTAL SYNTHESIS FROM CARBOCYCLIC PRECURSORS Punctatin A Acanthoic Acid Stachybocin Spirolactam Scabronine G Chapecoderin A Dragmacidin F Reserpine Fawcettimine Tamiflu Miscellanea TOTAL SYNTHESIS FROM LACTONE PRECURSORS Megaphone Dihydromevinolin Mennostatin A Furaquinocin C Miscellanea SINGLE TARGET-ORIENTED SYNTHESIS Synchronicity Joining Forces Back-to-Back Publishing Same Year Publications Single Target Molecules with Special Relevance Quinine Lactacystin Taxol MAN, MACHINE, AND VISUAL IMAGERY IN SYNTHESIS PLANNING The LHASA Program syngen wodca The CHIRON Program Computer-Aided Synthesis Planning THE ESSENCE OF SYNTHESIS - A RETROSPECTIVE Lest we Forget The Corey and Stork Schools The Visual Dialogue with Molecules Total Synthesis: From whence we came In Pursuit of the "Ideal Synthesis" For the Love of Synthesis (Synthephilia) Organic Synthesis: The where we are going (Quo vadis) Synthesis at the Service of Humankind From the Chiron Approach to Catalysis A Salute to the Vanguards of Synthesis