Alicyclic Compounds

A Modern Comprehensive Treatise

2nd Edition - January 1, 1974
Editor: M. F. Ansell
Language: English
eBook ISBN:
9 7 8 - 1 - 4 8 3 2 - 2 1 3 0 - 4

Supplements to the Second Edition of Rodd’s Chemistry of Carbon Compounds, Volume II: Alicyclic Compounds: Part C: Polycarbocyclic Compounds, Excluding Steroids covers the… Read more

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Supplements to the Second Edition of Rodd’s Chemistry of Carbon Compounds, Volume II: Alicyclic Compounds: Part C: Polycarbocyclic Compounds, Excluding Steroids covers the classification, natural products, and biogenesis of polycarbocyclic compounds. This book is divided into 11 chapters. Considerable chapters are devoted to the classification and nomenclature of polycarbocyclic compounds, including bicyclic monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, and triterpenoids. Other chapters deal with the classification and nomenclature of selective steroids, such as steroids, bile acids, sex hormones, saponins, and sapogenins. The concluding chapter highlights the biogenesis of terpenes and sterols. This book is an ideal source for organic chemists and researchers.

Preface

Official Publications; Scientific Journals and Periodicals

List of Common Abbreviations and Symbols Used

Chapter 9. Polycarbocyclic Compounds with Separate Ring-Systems, and Spiro Compounds

1. Introduction

2. Compounds with Rings Joined Directly or through a Carbon Chain

3. Spiro Compounds; Spirans

a. Preparative Methods

b. Properties

Chapter 10. Polycyclic Compounds. Fused or Condensed Cyclic Systems

1. The Bicyclo[1.1.0]Butane Group

2. The Bicyclo[2.1.0]Pentane Group

3. The Bicyclo[3.1.0]Hexane Group

4. The Bicyclo[4.1.0]Heptane Group

5. The Bicyclo[5.1.0]Octane Group

6. The Bicyclo[6.1.0]Nonane Group

7. The Bicyclo[2.2.0]Hexane Group

8. The Bicyclo[3.2.0]Heptane Group

9. The Bicyclo[4.2.0]Octane Group

10. The Bicyclo[6.2.0]Decane Group

11. The Bicyclo[3.3.0]Octane Group

12. The Bicyclo[4.3.0]Nonane Group

13. The Bicyclo[4.4.0]Decane Group

14. Highly Condensed Systems

Chapter 11. Polycarbocyclic Bridged Ring Compounds

1. Introduction

a. General Methods of Synthesis

b. Bredt's Rule

c. Bridged Carbonium Ions

d. Molecular Orbital Theory

e. Nuclear Magnetic Resonance Spectroscopy (n.m.r.)

f. Fluxional Molecules

2. The Bicyclo[1.1.1]Pentane Group

3. The Bicyclo[2.1.1]Hexane Group

Preparation

4. The Bicycloheptane Group

a. The Bicyclo[3.1.1]Heptane Group

b. The Bicyclo[2.2.1]Heptane Group

5. Polycyclic Compounds Derived from Cyclopentadiene

a. Oligomerisation Products of Cyclopentadiene

6. The Bi- and Tri-Cyclooctane Group

Mechanism and Structure

a. The Bicyclo[2.2.2]Octane Group

b. The Bicyclo[3.2.1]Octane Group

c. The Tricyclo[3.3.0.02,8]Octane Group

7. The Polycyclo[3.3.1]Nonane Group

a. The Bicyclo[3.3.1]Nonane Group

b. The Tricyclo[3.3.1.02,8]Nonane Group

c. The Tricyclo[3.3.1.03,7]Nonane Group

d. The Tetracyclo[3.3.1.02,8.04,6]Nonane, Triasterane, Group

8. The Bicyclo[3.2.2]Nonane Group

Preparation

9. The Bicyclo[4.2.1]Nonane Group

Preparation

10. The Bicyclo[4.2.2]Decane Group

Mechanism and Structure

Preparation

11. The Tricyclodecane Group

a. The Tricyclo[3.3.2.02,8]Decane Group

b. The Tricyclo[3.3.1.13,7]Decane, Adamantane, Group

12. The Bicyclo[3.3.3]Undecane Group

Chapter 12. Bicyclic Monoterpenoids

1. Introduction

2. The Thujane Group

3. The Carane Group

4. The Pinane Group

5. The Norbornane Group

a. Camphene and Related Compounds

b. Bornane (Camphane) Derivatives

c. Fenchane Derivatives

Chapter 13. The Sesquiterpenoids

1. Introduction

2. Acyclic Types

(i) Hydrocarbons

(ii) Oxygenated Derivatives

3. Monocyclic Types

4. Cyclopentylcyclohexanes

(i) Hydrocarbons

(ii) Oxygenated Derivatives

5. Bicyclo[4.1.0]Heptanes

(i) Hydrocarbons

(ii) Oxygenated Derivatives

6. Bicyclo[4.4.0]Decanes

(i) Hydrocarbons

(ii) Oxygenated Derivatives

7. Bicyclo[4.3.0]Nonanes

8. Bicyclo[5.3.0]Decanes

(i) Hydrocarbons

(ii) Oxygenated Derivatives

9. Spiro Compounds

(i) Hydrocarbons

(ii) Oxygenated Derivatives

10. Polycyclic Systems

(i) Hydrocarbons

(ii) Oxygenated Derivatives

11. Macrocyclic Sesquiterpenes

(i) Hydrocarbons

(ii) Oxygenated Derivatives

Chapter 14. Diterpenoids, Sesterterpenoids and Triterpenoids

1. Introduction

2. Diterpenoids

a. Bicyclic Diterpenoids

b. Tricyclic Diterpenoids

c. Tetracyclic Diterpenoids

d. The Cembrane Group

e. Eremolactone

3. Sesterterpenoids

4. Triterpenoids

(a) The Fusidanes

(b) Group A

(c) Group B

5. Laboratory Synthesis

a. Diterpenoids

b. Triterpenoids

Chapter 15. Steroids: Sterols and Bile Acids

1. Introduction

2. Geometry of the Steroid Nucleus

3. Structure in Relation to Physical Properties

4. Principal Chemical Reactions

(i) Color Reactions

(ii) The 3,5-Cyclosteroid Rearrangement and Related Reactions

(iii) Backbone Rearrangements and Related Reactions

(iv) Side-Chain Oxidation

(v) Epoxidation of Δ5-Stenols and Related Compounds

(vi) Reactions of 7-Dehydrosterols

(vii) Stanols

(viii) Stanones

(ix) Remote Oxidation

5. individual Sterols and Related Compounds

a. The Cholesterol Series

b. Ergosterol and Related Compounds

c. Other Sterols

d. Miscellaneous Structural Type

6. Bile Acids

Additions

Chapter 16. Steroids: Sex Hormones; Adrenocortical Hormones

1. Sex Hormones and Related Compounds

a. Oestrogens

b. The Gestogens

c. The Androgens

d. Homosteroids

e. Synthesis of Adrenocortical Steroids

2. Adrenocortical Hormones

d. Aldosterone

3. Cyclosteroids

4. Dimeric Steroid Hormones

5. Halogenated Steroids

a. Oestrogens

b. Androgens

c. Gestogens

6. Other Substituted Steroids

b. Pregnane Series

Chapter 17. Steroids: Cardiotonic Glycosides and Aglycons; Toad Poisons

Digoxin Derivatives

Digitoxigenin and Derivatives

Canarigenin (Δ4-Analogue of Digitoxigenin)

Uzarigenin and Related Compounds

Digitalis Glycosides and Aglycons

Digitoxigenone

Toad Poisons, etc

Chapter 18. Steroid Saponins and Sapogenins

1. The Saponins

2. The Sapogenins

Sources and Isolation

Biogenesis

Physical Properties

New Sapogenins

Aminospirostans

Reactions of the Sapogenin Side-Chain

Chapter 19. Biogenesis of Terpenes and Sterols

1. Introduction

2. Biosynthesis of Mevalonate (MVA)

3. Hemiterpenes

4. Monoterpenes

5. Sesquiterpenes

6. Diterpenes

8. Triterpenes

(i) General

(ii) Demethylation Reactions

(iii) Alkylation at C(24)

(iv) Insertion of Double Bonds

(v) Spirostanols

(vi) Cardenolides

(vii) Bufatenolides

(viii) Ecdysones

9. The Tetraterpenoids: the Carotenoids

(i) Prephytoene

(ii) Desaturation of Phytoene

(iii) Cyclisation of Lycopene

(iv) Xanthophyll Formation

(v) C45 and C50 Carotenoids

(vi) Biosynthesis in Photosynthetic Bacteria

10. Terpenoid Quinones

Index