Strategies and Tactics In Organic Synthesis

Strategies and Tactics In Organic Synthesis

1st Edition - January 1, 1984

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  • Editor: Thomas Lindberg
  • eBook ISBN: 9780323152938

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Strategies and Tactics in Organic Synthesis presents the chronological development of ideas and experimentation in organic synthesis. This book is organized into 13 chapters that explore the synthetic pathways of various organic compounds. The first four chapters describe the variations in the synthesis of superphane, gibberellic acid, prostaglandin, and alkaloids. The following chapters cover the organic synthesis and biosynthesis of tylonolide, endiandric acids A-G, dodecahedrane, fomannosin, and illudol. A chapter focuses on the evolution of the total synthesis of jatrophone, an architecturally interesting macrocyclic diterpene extracted from Jatropha gossypiifolia. Another chapter discusses the heuristic principle for the stereorationale design of alkaloid syntheses. The remaining chapters discuss the approach to the total synthesis of steroids, streptonigrin, methynolide, and Prelog-Djerassi lactonic acid. Organic chemists, teachers, and students will find this book of great value.

Table of Contents

  • Contributors


    1. Theme and Variations: A Synthesis of Superphane

    I. Introduction, Goals, and Synthetic Philosophy

    II. Theme

    III. Variations

    IV. A Synthesis of Superphane

    V. Further Variations


    2. The Total Synthesis of Gibberellic Acid

    I. Introduction

    II. The Synthetic Challenge

    III. The Synthetic Strategy

    IV. Preliminary Studies: Stereocontrolled Elaboration of the A Ring

    V. Model Studies: The Intramolecular Diels-Alder Strategy is Tested

    VI. Model Studies: A Method for the Construction of the C and D Rings

    VII. The Hydrindane Approach

    VIII. The Hydronaphthalene Approach: (1) The Advance to Chandra's Dione

    IX. The Hydronaphthalene Approach: (2) Operations on the C Ring

    X. The Hydronaphthalene Approach: (3) The D Ring

    XI. The Hydronaphthalene Approach: (4) Subjugation of the Β Ring

    XII. The Hydronaphthalene Approach: (5) The Triumph of the Intramolecular Diels-Alder Strategy

    XIII. The Hydronaphthalene Approach: (6) Stalemate at the A Ring

    XIV. The Total Synthesis of Gibberellic Acid


    3. A Prostaglandin Synthesis

    I. Introduction

    II. 7-Oxaprostaglandins

    III. Prostaglandin F2α

    IV. 13,14-Dehydroprostaglandins


    4. Synthesis of Indole Alkaloids

    I. Introduction

    II. Early Thoughts

    III. Initial Results: First Phase

    IV. Flexible Strategy-Flexible Tactics: Second Phase

    V. Synthesis of (±)-Aspidospermidine: Third Phase

    VI. Reverse Roles: Fourth Phase

    VII. Completion of the "Model Work"

    VIII. New Territory


    5. Synthesis of Tylonolide, the Aglycone of Tylosin

    I. Introduction

    II. General Strategy

    III. Preliminary Work

    IV. Synthesis

    V. Concluding Remarks


    6. Pericyclic Reactions in Organic Synthesis and Biosynthesis: Synthetic Adventures with Endiandric Acids A-G

    I. Introduction: The Appealing Endiandric Acid Cascade

    II. Retrosynthetic Analyis of Endiandric Acids A-G

    III. Synthesis of the Key Bicyclic Intermediate

    IV. Functionalization of the Bicyclic Intermediate: Synthesis of Endiandric Acids D, E, F, and G

    V. The Intramolecular Diels-Alder Reactions: Synthesis of Endiandric Acids A, B, and C

    VI. Conclusions


    7. Plato's Solid in a Retort: the Dodecahedrane Story

    I. Introduction

    II. The Decision against Convergency and Building of the Cornerstone

    III. A Retrosynthetic Glimpse and Symmetry Considerations

    IV. Arrival at the "Closed" and "Open" Dilactones

    V. Chemical Reactivity of the "Open" Dilactone

    VI. Functionalization Reactions of the "Closed" Dilactone

    VII. (C2)-Dioxa-C20-Octaquinane, a Heterocyclic Trisecododecahedrane

    VIII. The Pilot Photochemical Experiment

    IX. Trisecododecahedranes via Dichloro Diester Reduction

    X. The Monoseco Level of Elaboration

    XI. Installation of the Final Bond: Formation of 1,16-Dimethyldodecahedrane

    XII. Further Developments

    XIII. Controlled Monosubstitution and Isolation of an Isododecahedrane

    XIV. Bypassing the Unwanted Reaction Pathway

    XV. (CH)20: The Parent Dodecahedrane


    8. The Synthesis of Fomannosin and Illudol

    I. Introduction

    II. The Target

    III. The Ketene Cycloaddition Approach to Fomannosin

    IV. Synthesis of Illudol and Fomannosin from a Common Intermediate

    V. Summary


    9. Evolution of a Synthetic Strategy: Total Synthesis of Jatrophone

    I. Introduction

    II. General Background

    III. A Strategy for the Total Synthesis of Jatrophone

    IV. Synthesis of Simple 3(2H)-Furanones: The First Major Spin-Off of the Jatrophone Program

    V. A Successful Conclusion to Phase I: Synthesis of 3(2H)-Furanone 21

    VI. Synthesis of α-Hydroxymethylcyclopentenone: An Initial Solution

    VII. An Alternate Approach to α-Hydroxymethylcyclopentenone: Development of a Versatile Latent α-Ketovinyl Anion Equivalent

    VIII. Synthesis of the Pentenomycins, Their Epimers, and Dehydropentenomycin: A Major Diversion

    IX. Return to the Jatrophone Problem: A Successful Failure

    X. Development of An Alternative 3(2H)-Furanone Protocol: A New 1,3-Diketone Synthesis

    XL Exploitation of the Improved 3(2H)-Furanone Protocol

    XII. Macrocyclization: A Difficult Step

    XIII. Completion of Phase II: Synthesis of Normethyljatrophone

    XIV. Phase III: The Stereochemical Problem

    XV. Total Synthesis of Jatrophone and Its Epimer: The Final Goal

    XVI. Further Diversions during the Jatrophone Synthetic Program

    XVII. Reactions of Simple 3(2H)-Furanones and Furadienones with Propanethiol

    XVIII. Jatrophone Analogs: cis- and trans-Normethyljatropholactones

    XIX. Isolation of Three New Jatrophone Derivatives

    XX. Interplay of Structure and Conformation of the Jatrophone Nucleus vis-a-vis Antitumor Activity


    10. On the Stereochemistry of Nucleophilic Additions to Tetrahydropyridinium Salts: A Powerful Heuristic Principle for the Stereorationale Design of Alkaloid Syntheses



    11. A Nonbiomimetic Approach to the Total Synthesis of Steroids: the Transition Metalcatalyzed Cyclization of Alkenes and Alkynes

    I. Introduction

    II. Model Studies in Cobalt-Mediated Alkyne Cyclizations

    III. Cobalt-Mediated [2 + 2 + 2]Cycloadditions en Route to Annulated Cyclohexadienes


    12. Evolution of a Strategy for Total Synthesis of Streptonigrin

    I. Introduction

    II. Synthetic Strategy

    III. Preliminary AB-Ring Studies

    IV. Preliminary CD-Ring Studies

    V. Synthesis of Streptonigrin


    13. Methynolide and the Prelog-Djerassi Lactonic Acid: an Exercise in Stereocontrolled Synthesis

    I. Introduction

    II. Excursions from 2,4-Dimethylfuran

    III. Further Expeditions from 8-Oxabicyclo[3.2.1]octanes

    IV. The Prelog-Djerassi Lactonic Acid (4)

    V. A Cycloheptanoid Route to Methynolide



Product details

  • No. of pages: 384
  • Language: English
  • Copyright: © Academic Press 1984
  • Published: January 1, 1984
  • Imprint: Academic Press
  • eBook ISBN: 9780323152938

About the Editor

Thomas Lindberg

Affiliations and Expertise

G. D. Searle Research and Development

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