Alicyclic Compounds

Alicyclic Compounds; Six- and Higher-Membered Monocarbocyclic Compounds (Partial)

Poiycarbocyclic Compounds excluding Steroids

Steroids

List of Contributors

Preface

List of Common Abbreviations and Symbols Used

Chapter 6. Acyclic and Monocyclic Monoterpenoids


1. Introduction


2. Artemisyl, Santolinyl, Chrysanthemyl and Other Irregular Systems


3. 2,6-Dimethyloctanes


4. Naturally-Occurring Halogenated Monoterpenoids


5. Cyclobutanes


6. Cyclopentanes


7. Tetramethylcyclohexanes


8. Menthanes

(a) o-Menthanes

(b) m-Menthanes

(c) p-Menthanes

Chapter 7. The Carotenoid Group of Natural Products


1. Scope of Presentation


2. Relevant Literature Overviews


3. Trends in Carotenoid Chemical Research


4. Improved Methodology

(a) Isolation and Chromatography

(b) NMR-Spectroscopy

(c) Circular Dichroism

(d) Other Spectroscopic Techniques


5. Partial and Total Synthesis


6. New Structures

(a) Higher Carotenoids (C45, C50)

(b) Nor-Carotenoids

(c) Apo-Carotenoids (C<40)

(d) C30-Carotenoids (diapo)

(e) Sulfates

(f) Glycosides and Glycosyl Esters

(g) Epoxides and Oxabicycloheptanes

(h) In-Chain-Methyl Oxidized Carotenoids

(i) Alienes

(j) Acetylenes

(k) 7,8-Dihydrocarotenoids

(l) Other Carotenes and Xanthophylls

(m) Carotenoproteins


7. Optical Isomerism including Aliene Isomerism


8. Geometrical Isomerism


9. Artifacts


10. Interdisciplinary Fields

(a) Biosynthesis

(b) Chemosystematics

(c) Metabolism

(d) Functions

(e) Photochemistry and Photoprotection

(f) Vision

(g) Aquaculture

(h) Medical Applications

Chapter 8a. The Cycloheptanes and Cyclooctanes


1. Introduction


2. Preparation of Cycloheptanes and Cyclooctanes

(a) Ring Expansion Methods

(b) Cyclisation Reactions

(c) Functional Group Modification


3. Properties and Reactions

(a) Conformation and Structure

(b) Reactions


4. Biochemistry

Chapter 8b. Large Alicyclic Ring Systems


1. Introduction


2. Preparation of Macrocyclic Hydrocarbons

(a) Ring Expansion Methods

(b) Ring Contraction Methods

(c) Cyclisation Reactions

(d) Functional Group Modification


3. Properties and Reactions

(a) Conformation and Structure

(b) Transannular Reactions

(c) Complex Formation


4. Biochemistry

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


1. Introduction


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

(a) Polycyclopropanes and Polycyclopropenes

(b) Cyclopropylcyclobutanes and Cyclopropylbutenes

(c) Polycyclobutanes

(d) Polycyclopentanes and Polycyclopentenes

(e) Cyclopropylcyclopentanes and Cyclopropylcyclopentenes

(f) Cyclopropylcyclohexanes

(g) Cyclobutylcyclohexanes

(h) Cyclopentylcyclohexanes

(i) Polycyclohexanes and Polycyclohexenes

(j) Cyclopentylcycloheptanes and Cyclopentylcycloheptenes

(k) Cyclohexylcycloheptadienes

(l) Polycycloheptenes

(m) Miscellaneous Bicyclic Compounds


3. Spiro Compounds; Spiranes

(a) The Spiro[2,2]Pentane Group

(b) The Spiro[2,3]Hexane Group

(c) The Spiro[2,4]Heptane Group

(d) The Spiro[2,5]Octane Group

(e) The Spiro[2,6]Nonane Group

(f) The Spiro[3,3]Heptane Group

(g) The Spiro[3,4]Octane Group

(h) The Spiro[3,5]Nonane Group

(i) The Spiro[4,4]Nonane Group

(j) The Spiro[4,5]Decane Group

(k) The Spiro[5,5]Undecane Group

(l) Miscellaneous Groups

(m) Polyspiranes

Chapter 10. Polycyclic Compounds. Fused or Condensed Cyclic Systems


1. Bicyclo[n.1.O]Alkanes

(a) General Physical and Spectroscopic Properties

(b) General Chemical Reactions


2. Bicyclo[n.1.0]alk-2-enes

(a) Synthesis


3. The Bicyclo[1.1.0]Butane Group

(a) Synthesis

(b) Reactions


4. Bicyclo[2.1.0]Pentane

(a) General Properties

(b) Reactions


5. Bicyclo[3.1.0]Hexanes

(a) Synthesis

(b) Structure and Spectra

(c) Chemical Reactions


6. Bicyclo[4.1.0]Heptanes

(a) Synthesis

(b) Structure

(c) Reactions


7. Bicyclo[5.1.0]Octanes and Bicyclo[6.1.0]Nonanes

(a) Structure and Physical Properties

(b) Synthesis

(c) Reactions


8. Bicyclo[7.1.0]Decene


9. Bicyclo[10.1.0]Tridecane


10. Bicyclo[m.n.0]Alkanes

(a) Spectrometry, Spectroscopy and General Chemistry


11. Bicyclo[2.2.0]Hexanes and Bicyclo[3.2.0]Heptanes

(a) Structure

(b) Reactions


12. Bicyclo[2.2.0]Hexenes and Bicyclo[3.2.0]Heptenes


13. Bicyclo[4.2.0]Octanes and Bicyclo[5.2.0]Nonanes


14. Bicyclo[3.3.0]Octane (Hexahydropentalene)


15. Bicyclo[4.30]Nonane (Octahydro-1H-Indene), Bicyclo[5.3.0]Decane (Decahydroazulene), and Bicyclo[6.3.0]Undecane


16. Bicyclo[4.4.0]Decanes (Decalins)

(a) Structure and Stereochemistry

(b) Reactions

Addendum

(a) Bicyclo[3.3.0]Octane Group

(b) Bicyclo[4.3.0]Nonanes, Bicyclo[4.4.0]Decanes, Bicyclo[3.1.0]Hexanes, and Bicyclo[4.1.0]Heptanes

Chapter 11. Poiycarbocyclic Bridged Ring Compounds


1. Introduction


2. General Methods of Synthesis

(a) Prom Simple Monocyclic and Nonbridged Polycyclic Compounds

(b) Elaboration of Bridged Bicyclic and Tricyclic Compounds into Higher Polycyclics


3. Strained Poiycarbocyclic Alkenes

(a) Syntheses of Anti-Bredt Systems

(b) Syntheses of Pyramidalized Alkenes


4. Special Topics

(a) Propellanes

(b) The Tricyclo[3.3.1.13,7]Decane (Adamantane) Group


5. Acknowledgment

Chapter 12. Bicarbocyclic Natural Products


1. Introduction


2. The Thujane Group

(a) Hydrocarbons

(b) Alcohols

(c) Ketones


3. The Carane Group

(a) Hydrocarbons

(b) Alcohols and Epoxides

(c) Ketones

(d) Carboxylic Acids

(e) Halogeno and Cyano Derivatives

(f) Norcaranes and Norcarenes


4. The Wagner-Meerwein Rearrangement


5. The Pinane Group

(a) Hydrocarbons

(b) Epoxides, Alcohols, Aldehydes, Ketones, and Acids

(c) Halogeno, Amino, and Other Derivatives


6. Tricyclene


7. The Norbomane Group: Camphor and Related Compounds

(a) Camphene and Related Compounds

(b) Camphor, Epicamphor and Related Compounds

(c) Alcohols

(d) Bases of Bornane Series


8. The Norbomane Group: Fenchone and Related Compounds

(a) Ketones and Alcohols

(b) Hydrocarbons

Chapter 13. The Sesquiterpenoids


1. Introduction


2. Acyclic Compounds


3. Monocyclic Compounds


4. Bicyclo[4.4,0]Decanes


5. Bicyclo[4.3.0]Nonanes


6. Cyclopentyl Cyclohexanes


7. Spiro Compounds


8. Bicyclo[5.3.0]Decanes


9. Macrocyclic Compounds


10. Triquinanes


11. Other Polycyclic Systems

Chapter 14. Diterpenoids and Sesterterpenoids


1. Introduction


2. Acyclic and Related Diterpenoids


3. Bicyclic Diterpenoids

(a) Labdanes

(b) Clerodanes


4. Tricyclic Diterpenoids


5. Tetracyclic Diterpenoids

(a) Kaurenes

(b) Gibberellins

(c) Atiserenes, Beyerenes and Trachylobanes

(d) Aphidicolin and Stemaranes


6. Cembranes


7. Miscellaneous Diterpenoids


8. Sesterterpenoids

Chapter 15, Steroids


1. Introduction


2. Technical Steroid Synthesis

(a) Corticosteroid Synthesis

(b) Synthesis of 19-Norsteroids


3. Steroid Total Synthesis

(a) Intramolecular Diels-Alder Cycloadditions

(b) Intermolecular Diels-Alder Cycloadditions

(c) Asymmetric Cyclizations

(d) Free-Radical Cyclizations

(e) Cationic Cyclizations


4. Remote Functionalization of Non-Activated Positions in Steroids


5. The Brassinosteroids

(a) Introduction

(b) Synthesis of Brassinosteroids


6. Synthesis of Vitamin D and Analogues

(a) Introduction

(b) Partial Syntheses Starting with Cholesterol or Ergosterol

(c) Microbiological Route to 1α-Hydroxy Derivatives

(d) Introduction of the 1α-Hydroxyl Group in the Secotriene Stage

(e) Convergent Syntheses of Vitamin D and Analogues


7. Biosynthesis of the Steroids

Chapter 16. Glycosides, Saponins and Sapogenins


1. Isolation

(a) Structure Elucidation

(b) Mass Spectroscopy

(c) NMR Spectroscopy

(d) X-Ray Crystallography


2. Biological Activity

(a) Action on Metabolism

(b) Antitumour and Antileukemic Activity

(c) Antimicrobial Activity

(d) Mollusciddal Activity

(e) Miscellaneous


3. Biogenesis


4. Steroid Saponins and Sapogenins

(a) Saponins

(b) Sapogenins

(c) References

(d) Nomenclature and Configuration

(e) Triterpenoid Saponins and Sapogenins

(f) Synthesis

(g) Production of Saponins by Cell Culture

Chapter 17. Triterpenoids


1. The Squalene Group


2. The Lanostane Group


3. The Dammarane Group


4. The Baccharane/Shionane Group


5. The Lupane Group


6. The Oleanane Group


7. The Ursane Group


8. The Hopane Group


9. The Stictane Group


10. Miscellaneous

Guide to the Index

Index