Terpenes: Flavors, Fragrances, Pharmaca, Pheromones Book

Preface     IX
Terpenes: Importance, General Structure, and Biosynthesis     1
Term and Significance     1
General Structure: The Isoprene Rule     2
Biosynthesis     3
Hemi- and Monoterpenes     10
Hemiterpenes     10
Acyclic Monoterpenes     10
Monocyclic Monoterpenes     13
Cyclopropane and Cyclobutane Monoterpenes     13
Cyclopentane Monoterpenes     14
Cyclohexane Monoterpenes     15
Cymenes     18
Bicyclic Monoterpenes     19
Survey     19
Caranes and Thujanes     20
Pinanes     20
Camphanes and Fenchanes     21
Cannabinoids     22
Sesquiterpenes     24
Farnesanes     24
Monocyclic Farnesane Sesquiterpenes     25
Cyclofarnesanes and Bisabolanes     25
Germacranes and Elemanes     26
Humulanes     27
Polycyclic Farnesane Sesquiterpenes     28
Caryophyllanes     28
Eudesmanes and Furanoeudesmanes     29
Eremophilanes, Furanoeremonphilanes, Valeranes     31
Cadinanes     34
Drimanes     36
Guaianes and Cycloguaianes     37
Himachalanes, Longipinanes, Longifolanes     41
Picrotoxanes     42
Isodaucanes and Daucanes     42
Protoilludanes, Illudanes, Illudalanes     43
Marasmanes, Isolactaranes, Lactaranes, Sterpuranes     44
Acoranes     45
Chamigranes     45
Cedranes and Isocedranes     46
Zizaanes and Prezizaanes     47
Campherenanes and Santalanes     47
Thujopsanes     49
Hirsutanes     49
Other Polycyclic Sesquiterpenes     50
Pinguisanes     50
Presilphiperfolianes, Silphiperfolianes, Silphinanes, Isocomanes     50
Diterpenes     52
Phytanes     52
Cyclophytanes     52
Bicyclophytanes     54
Labdanes     54
Rearranged Labdanes     55
Tricyclophytanes     57
Pimaranes and Isopimaranes     57
Cassanes, Cleistanthanes, Isocopalanes     59
Abietanes and Totaranes     61
Tetracyclophytanes     63
Survey     63
Beyeranes      64
Kauranes and Villanovanes     64
Atisanes     66
Gibberellanes     66
Grayanatoxanes     67
Cembranes and Cyclocembranes     68
Survey     68
Cembranes     70
Casbanes     71
Lathyranes     71
Jatrophanes     72
Tiglianes     72
Rhamnofolanes and Daphnanes     73
Eunicellanes and Asbestinanes     73
Biaranes     74
Dolabellanes     74
Dolastanes     75
Fusicoccanes     75
Verticillanes and Taxanes     75
Trinervitanes and Kempanes     76
Prenylsesquiterpenes     77
Xenicanes and Xeniaphyllanes     78
Prenylgermacranes and Lobanes     78
Prenyleudesmanes and Bifloranes     79
Sacculatanes (Prenyldrimanes)     80
Prenylguaianes and Prenylaromadendranes     80
Sphenolobanes (Prenyldaucanes)     81
Ginkgolides     81
Sesterterpenes     82
Acyclic Sesterterpenes     82
Monocyclic Sesterterpenes     82
Polycyclic Sesterterpenes     83
Bicyclic Sesterterpenes     83
Tricyclic Sesterterpenes     84
Tetra- and Pentacyclic Sesterterpenes     85
Triterpenes     86
Linear Triterpenes     86
Tetracyclic Triterpenes, Gonane Type     88
Survey     88
Protostanes and Fusidanes     89
Dammaranes     89
Apotirucallanes     91
Tirucallanes and Euphanes     91
Lanostanes     92
Cycloartanes     93
Cucurbitanes     94
Pentacyclic Triterpenes, Baccharane Type     95
Survey     95
Baccharanes and Lupanes     97
Oleananes     97
Taraxeranes, Multifloranes, Baueranes     98
Glutinanes, Friedelanes, Pachysananes     99
Taraxastanes and Ursanes     100
Pentacyclic Triterpenes, Hopane Type     101
Survey     101
Hopanes and Neohopanes     102
Fernanes     103
Adiananes and Filicanes     104
Gammaceranes     104
Other Pentacyclic Triterpenes     105
Survey     105
Stictanes and Arboranes     106
Onoceranes and Serratanes      106
Iridals     107
Tetraterpenes     109
Carotenoids     109
Apocarotenoids     111
Diapocarotenoids     112
Megastigmanes     113
Polyterpenes and Prenylquinones     115
Polyterpenes     115
Prenylquinones     116
Selected Syntheses of Terpenes     119
Monoterpenes     119
Concept of Industrial Syntheses of Monoterpenoid Fragrances     119
(R)-(+)-Citronellal     121
Rose oxide     121
Chrysanthemic Acid Methyl Ester     122
[alpha]-Terpineol     123
(1R,3R,4S)-(-)-Menthol     124
Camphor from [alpha]-Pinene     124
[alpha]-Pinene and Derivatives for Stereospecific Syntheses of Chiral Monoterpenes     126
Hexahydrocannabinol     128
Sesquiterpenes     129
[Beta]-Selinene     129
Isocomene     130
Cedrene     132
Periplanone B     135
Diterpenes     138
Vitamin A (Retinol Acetate)     138
Cafestol     141
Baccatin III as the Precursor of Taxol     145
Triterpenes      152
Lupeol     152
Isolation and Structure Elucidation     160
Isolation from Plants     160
Spectroscopic Methods of Structure Elucidation     160
Structure Elucidation of a Sesquiterpene     161
Double Bond Equivalents     161
Functional Groups and Partial Structures detected by [superscript 13]C NMR     162
Skeletal Structure (Connectivities of Atoms)     163
Relative Configuration     169
Absolute Configuration     171
Determination of the Crystal Structure     173
Molecular Structure and Odor of Terpenes     176
Bibliography     180
Survey of Important Parent Skeletons of Terpenes     185
Subject Index     197