The Logic of Chemical Synthesis

Автор(ы):Corey E. J., Xue-Min Cheng
06.10.2007
Год изд.:1989
Описание: The title of this three-part volume derives from a key theme of the book—the logic underlying the rational analysis of complex synthetic problems. Although the book deals almost exclusively with molecules of biological origin, which are ideal for developing the fundamental ideas of multistep synthetic design because of their architectural complexity and variety, the approach taken is fully applicable to other types of carbon-based structures. Part One outlines the basic concepts of retrosynthetic analysis and the general strategies for generating possible synthetic pathways by systematic reduction of molecular complexity. Part Two, a collection of multistep syntheses accomplished over a period of more than three decades by the Corey group, provides much integrated information on synthetic methods and pathways for the construction of interesting target molecules. Part Three is intended to balance the coverage of Parts One and Two and to serve as a convenient guide to the now enormous literature of multistep synthesis. Information on more than five hundred interesting multistep syntheses of biologically derived molecules is included. It is hoped that the structural range and variety of target molecules presented in Part Three will appeal to many chemists. Synthesis remains a dynamic and central area of chemistry. There are many new principles, strategies and methods of synthesis waiting to be discovered. If this volume is helpful to our many colleagues in the chemical world in their pursuit of discovery and new knowledge, a major objective of this book will have been met.
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CONTENTS OF PART ONE GENERAL APPROACHES TO THE ANALYSIS OF COMPLEX SYNTHETIC PROBLEMS
  CHAPTER ONE The Basis for Retrosynthetic Analysis
    1.1 Multistep Chemical Synthesis [1]
    1.2 Molecular Complexity [2]
    1.3 Thinking About Synthesis [3]
    1.4 Retrosynthetic Analysis [5]
    1.5 Transforms and Retrons [6]
    1.6 Types of Transforms [9]
    1.7 Selecting Transforms [15]
    1.8 Types of Strategies for Retrosynthetic Analyses [15]
  CHAPTER TWO Transform-Based Strategies
    2.1 Transform-Guided Retrosynthetic Search [17]
    2.2 Diels-Alder Cycloaddition as a T-Goal [18]
    2.3 Retrosynthetic Analysis of Fumagillol (37) [19]
    2.4 Retrosynthetic Analysis of Ibogamine (49) [22]
    2.5 Retrosynthetic Analysis of Estrone (54) [23]
    2.6 Retrosynthetic Analysis by Computer Under T-Goal Guidance [23]
    2.7 Retrosynthetic Analysis of Squalene (57) [25]
    2.8 Enantioselective Transforms as T-Goals [26]
    2.9 Mechanistic Transform Application [28]
    2.10 T-Goal Search Using Tactical Combinations of Transforms [31]
  CHAPTER THREE Structure-Based and Topological Strategies
    3.1 Structure-goal (S-goal) Strategies [33]
    3.2 Topological Strategies [37]
    3.3 Acyclic Strategic Disconnections [37]
    3.4 Ring-Bond Disconnections—Isolated Rings [38]
    3.5 Disconnection of Fused-Ring Systems [39]
    3.6 Disconnection of Bridged-Ring Systems [42]
    3.7 Disconnection of Spiro Systems [43]
    3.8 Application of Rearrangement Transforms as a Topological Strategy [44]
    3.9 Symmetry and Strategic Disconnections [44]
  CHAPTER FOUR Stereochemical Strategies
    4.1 Stereochemical Simplification—Transform Stereoselectivity [47]
    4.2 Stereochemical Complexity—Clearable Stereocenters [51]
    4.3 Stereochemical Strategies—Polycyclic Systems [54]
    4.4 Stereochemical Strategies—Acyclic Systems [56]
  CHAPTER FIVE Functional Group-Based and Other Strategies
    5.1 Functional Groups as Elements of Complexity and Strategy [59]
    5.2 Functional Group-Keyed Skeletal Disconnections [60]
    5.3 Disconnection Using Tactical Sets of Functional Group-Keyed Transforms [62]
    5.4 Strategic Use of Functional Group Equivalents [64]
    5.5 Acyclic Core Group Equivalents of Cyclic Functional Groups [67]
    5.6 Functional Group-Keyed Removal of Functionality and Stereocenters [68]
    5.7 Functional Groups and Appendages as Keys for Connective Transforms [71]
    5.8 Functional Group-Keyed Appendage Disconnection [75]
    5.9 Strategies External to the Target Structure [76]
    5.10 Optimization of a Synthetic Sequence [78]
  CHAPTER SIX Concurrent Use of Several Strategies
    6.1 Multistrategic Retrosynthetic Analysis of Longifolene (215) [81]
    6.2 Multistrategic Retrosynthetic Analysis of Porantherine (222) [83]
    6.3 Multistrategic Retrosynthetic Analysis of Perhydrohistrionicotoxin (228) [83]
    6.4 Multistrategic Retrosynthetic Analysis of Gibberellic Acid (236) [84]
    6.5 Multistrategic Retrosynthetic Analysis of Picrotoxinin (251) [86]
    6.6 Multistrategic Retrosynthetic Analysis of Retigeranic Acid (263) [88]
    6.7 Multistrategic Retrosynthetic Analysis of Ginkgolide В (272) [89]
    References [92]
    Glossary of Terms [96]
CONTENTS OF PART TWO SPECIFIC PATHWAYS FOR THE SYNTHESIS OF COMPLEX MOLECULES
    Introduction [99]
    Abbreviations [100]
  CHAPTER SEVEN Macrocyclic Structures
    7.1 Erythronolide В [104]
    7.2 Erythronolide A [108]
    7.3 Recifeiolide [112]
    7.4 Vermiculine [113]
    7.5 Enterobactin [114]
    7.6 N-Methylmaysenine [116]
    7.7 (-)-N-Methylmaysenine [120]
    7.8 Maytansine [122]
    7.9 Brefeldin A [124]
    7.10 Aplasmomycin [128]
  CHAPTER EIGHT Heterocyclic Structures
    8.1 Perhydrohistrionicotoxin [136]
    8.2 Porantherine [138]
    8.3 Biotin [140]
    8.4 Methoxatin [141]
    8.5 20-(S)-Camptothecin [143]
  CHAPTER NINE Sesquiterpenoids
    9.1 Insect Juvenile Hormones and Farnesol [146]
    9.2 Longifolene [151]
    9.3 Caryophyllenes [153]
    9.4 Caryophyllene Alcohol [155]
    9.5 Cedrene and Cedrol [156]
    9.6 Humulene [159]
    9.7 Dihydrocostunolide [161]
    9.8 Elemol [162]
    9.9 Helminthosporal [163]
    9.10 Sirenin [165]
    9.11 Sesquicarene [168]
    9.12 Copaeneand Ylangene [170]
    9.13 Occidentalol [172]
    9.14 Bergamotene [173]
    9.15 Fumagillin [174]
    9.16 Ovalicin [176]
    9.17 Picrotoxinin and Picrotin [178]
    9.18 Isocyanopupukeananes [180]
    9.19 Bisabolenes [183]
  CHAPTER TEN Polycyclic Isoprenoids
    10.1 Aphidicolin [188]
    10.2 Stemodinone and Stemodin [191]
    10.3 K-76 [193]
    10.4 Tricyclohexaprenol [195]
    10.5 Atractyligenin [198]
    10.6 Cafestol [201]
    10.7 Kahweol [204]
    10.8 Gibberellic Acid [205]
    10.9 Antheridic Acid [212]
    10.10 Retigeranic Acid [215]
    10.11 Diisocyanoadociane [218]
    10.12 Ginkgolide В and Ginkgolide A [221]
    10.13 Bilobalide [227]
    10.14 Forskolin [230]
    10.15 Venustatriol [234]
    10.16 Pseudopterosin A [237]
    10.17 (?)-Amyrin [239]
    10.18 (?)-Amyrin [241]
    10.19 Pentacyclosqualene [243]
    10.20 Dihydroconessine [246]
  CHAPTER ELEVEN Prostanoids
    11.1 Structures of Prostaglandins (PC(?)s) [250]
    11.2 (±)-Prostaglandins EI, Fia, Fip, AI and BI [251]
    11.3 Prostaglandins E(?), F( ?)and Their 11-Epimers [253]
    11.4 General Synthesis of Prostaglandins [255]
    11.5 Refinements of the General Synthesis of Prostaglandins [258]
    11.6 Prostaglandins (?) and (?) [262]
    11.7 Modified Bicyclo[2.2.1]heptane Routes to Prostaglandins [265]
    11.8 Synthesis of Prostaglandin AI and Conversion to Other Prostaglandins [267]
    11.9 Alternative Synthesis of Prostaglandins F(?) and E(?) [272]
    11.10 Conjugate Addition-Alkylation Route to Prostaglandins [273]
    11.11 Bicyclo[3.1.0]hexane Routes to Prostaglandins [276]
    11.12 Prostaglandin F(?) from a 2-OxabicycIo[3.3.0]octenone [278]
    11.13 11-Desoxy prostaglandins [280]
    11.14 Prostacycline (PGI2) [282]
    11.15 Major Human Urinary Metabolite of Prostaglandin D2 [284]
    11.16 Analogs of the Prostaglandin Endoperoxide PGH2 [286]
    11.17 12-Methylprostaglandin A2 and 8-Methylprostaglandin C2 [291]
    11.18 Synthesis of Two Stable Analogs of Thromboxane A2 [293]
    11.19 Synthesis of (±)-Thromboxane B2 [295]
    11.20 Synthesis of Prostaglandins via an Endoperoxide Intermediate. Stereochemical Divergence of Enzymatic and Biomimetic Chemical Cyclization Reactions [297]
    11.21 (±)-ClavuIone I and (±)-Clavulone II [303]
    11.22 (-)-Preclavulone-A [305]
    11.23 Hybridalactone [307]
  CHAPTER TWELVE Leukotrienes and Other Bioactive Polyenes
    12.1 Formation of Leukotrienes from Arachidonic Acid [312]
    12.2 Leukotriene A4 [313]
    12.3 Leukotriene C4 and Leukotriene D4 [318]
    12.4 Leukotriene B4 [320]
    12.5 Synthesis of Stereoisomers of Leukotriene B4 [324]
    12.6 Leukotriene B5 [328]
    12.7 5-Desoxyleukotriene D4 [330]
    12.8 Synthesis of the 11,12-Oxido and 14,15-Oxido Analogs of Leukotriene A4 and the Corresponding Analogs of Leukotriene C4 and Leukotriene D4 [331]
    12.9 12-H ydroxy-5,8,14-(Z)-10-(E)-eicosatetraenoic Acid (12-HETE) [334]
    12.10 Hepoxylins and Related Metabolites of Arachidonic Acid [337]
    12.11 Synthesis of 5-, 11-, and 15-HETE's. Conversion of HETE's into the Corresponding HPETE's [339]
    12.12 Selective Epoxidation of Arachidonic Acid [343]
    12.13 Synthesis of Irreversible Inhibitors of Eicosanoid Biosynthesis, 5,6-, 8,9-, and 11,12-Dehydroarachidonic Acid [345]
    12.14 Synthesis of a Class of Sulfur-Containing Lipoxygenase Inhibitors [351]
    12.15 Synthesis of a Putative Precursor of the Lipoxins [353]
    12.16 Bongkrekic Acid [355]
CONTENTS OF PART THREE GUIDE TO THE ORIGINAL LITERATURE OF MULTISTEP SYNTHESIS
  CHAPTER THIRTEEN
    13.1 Introduction [359]
    13.2 Abbreviations of Journal Names [361]
    13.3 Acyclic and Monocarbocyclic Structures [362]
    13.4 Fused-Ring Bi- and Tricarbocyclic Structures [366]
    13.5 Bridged-Ring Carbocyclic Structures [377]
    13.6 Higher Terpenoids and Steroids [384]
    13.7 Nitrogen Heterocycles (Non-bridged, Non-indole) [387]
    13.8 Fused-Ring Indole Alkaloids [395]
    13.9 Bridged-Ring Indole Alkaloids [399]
    13.10 Bridged-Ring Non-indole Alkaloids; Porphrins [403]
    13.11 Polycyclic Benzenoid Structures [407]
    13.12 Oxygen Heterocycles [410]
    13.13 Macrocylic Lactones [417]
    13.14 Macrocylic Lactams [422]
    13.15 Polyethers [425]
Index [427]
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