Description
Wiley Design and Strategy in Organic Synthesis From the Chiron Approach to Catalysis 2013 Edition by Stephen Hanessian, Simon Giroux, Bradley L. Merner
This long-awaited graduate level book, written by one of the world's leading organic chemists in collaboration with two of his former and present coworkers, adopts a refreshingly unique approach to synthesis planning and execution. Following an introductory look at the concept of synthesis, the authors discuss the Why, What, and How of organic synthesis as they apply to natural products. Although emphasis is on the Chiron Approach utilizing amino-acids, carbohydrates, hydroxy acids, terpenes, lactones and other naturally occurring small molecules as starting materials, catalytic asymmetric methods are also included as a corollary whenever relevant. A must-have source of first class information for everyone working in organic synthesis, be it in academia or industry. With a foreword by Larry E. Overman and David W. C. MacMillan Table of contents : - PREFACE 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 ... or Just Arrived The Futility of it All Synthesis as a Seeker of the Truth Nature as the Ultimate Synthesizer A Brave New Chemical World Exploring New Synthetic Methods THE 'WHAT' OF SYNTHESIS Periods, Trends, and Incentives A Century of Synthesis We the 'Synthesis 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 Kinetic Resolution (DKR) 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 alpha-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 ALPHA-AMINO ACID PRECURSORS Actinobolin Aspochalasin B Cephalotaxine 329 Alpha-Kainic Acid (W. Oppolzer) Alpha-Kainic Acid (P. T. Gallagher) Croomine Biotin Salinosporamide A Thienamycin FR901483 Tuberostemonine Phyllanthine Oscillarin ent-Cyclizidine Pactamycin Miscellanea TOTAL SYNTHESIS FROM CARBOHYDRATE PRECURSORS Ajmalicine ent-Actinobolin Trehazolin and Trehazolamine Fomannosin 9a-Desmethoxy Mitomycin A Saxitoxin and ss-Saxitoxinol ent-Decarbamoyl Saxitoxin Zaragozic acid A Hemibrevetoxin B Carbohydrates in Synthesis and in Biology Miscellanea TOTAL SYNTHESIS FROM HYDROXY ACIDS Griseoviridin Halicholactone Brasilenyne Octalactin A (3Z)-Dactomelyne UCS1025A Jerangolid A Miscellanea TOTAL SYNTHESIS FROM TERPENES Picrotoxinin Eucannabinolide Trilobolide and Thapsivillosin F Briarellin E and F Samaderine 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 WITH LACTONES AS PRECURSORS Megaphone Dihydromevinolin Mannostatin A Furaquinocin C Miscellanea SINGLE TARGET MOLECULE-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: To where we are going Synthesis at the Service of Humankind From the Chiron Approach to Catalysis A Salute to the Vanguards of Synthesis