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The Chemistry of Heterocyclic Compounds, Volume 23: Furopyrans and Furopyrones

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The Chemistry of Heterocyclic Compounds, Volume 23: Furopyrans and Furopyrones

Ahmed Mustafa (Editor)

ISBN: 978-0-470-18835-4 September 2009 376 Pages

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Description

The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects – properties, synthesis, reactions, physiological and industrial significance – of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.

I. Furopyrans and -pyrones 1

I. Naturally Occurring Furopyrans 2

1. Flumericin 2

2. Anhydrotetrahydroaucubigenin 9

II. Synthetic Furopyrans and-pyrones 11

III. References 13

II. Furocoumarins 14

I. Isolation 15

II. Physical Properties 32

III. Nomenclature 35

IV. Naturally Occurring Furocoumarins 35

1. Structure and Chemical Properties 35

A. Angelicin 36

B. Psoralen 38

C. Bergapten 41

D. Bergaptol 44

E. Isobergapten 44

F. Bergamottin 45

G. Xanthotoxin 46

H. Xanthotoxol 52

I. Isoimperatorin 52

J. Oxypeucedanin 52

K. Ostruthol 53

L. Imperatorin 55

M. Alloimperatorin 56

N. Heraclenin 56

O. Isopimpinellin 56

P. PheUopterin 58

Q. Byakangelicol 59

R. Byakangelicin 61

S. Pimpinellin 61

T. Sphondin 62

U. Halfordin and Isohalfordin 62

V. Nodakenetin 65

W. Peucedanin 69

X. Athamantin 70

Y. Discophoridin 72

Z. Edultin 73

AA. Peulustrin 73

BB. Columbianadin and Columbianin 76

CC. Archangelioin 77

DD. Archangelin 78

EE. Pyrocanesein 78

FF. 4,5',8-Trimethylpsoralen 79

GG. Aflatoxins B and G 79

2. Configuration 80

3. Biosynthesis 82

A. α-(/J'-Hydroxypropyl)dihydrofurans and a-Isopropenyl-dihydrofurans 83

B. α-IsopropyljS-hydroxyfurans and Relations 84

C. Simple Furans 86

4. Physiological Activity 87

V. References 90

III. Furochromones 102

I. Isolation 102

II. Physical Properties 103

III. Nomenclature 104

IV. Naturally Occurring Furochromones 104

1. Chemical Properties 104

A. Khellin 104

(1) Synthesis of khellin 107

(2) Synthesis of khellin analogs 112

(3) Reactions 112

B. Visnagin 133

(1) Synthesis of visnagin 134

(2) Synthesis of visnagin analogs and related transformations 136

(3) Reactions 138

C. Khellinol 143

D. Khetlinin 144

E. Khellol 145

F. Ammiol 147

G. Visamminol 148

2. Color Reactions 150

3. Physiological Activity 151

V. References 153

IV. Furoxanthones 160

I. Naturally Occurring Furoxanthones 160

1. Sterigmatocystin 160

II. Synthetic Furoxanthones 169

III. References 174

V. Furoflavones 175

I. Isolation 175

II. Physical Properties 175

III. Naturally Occurring Furoflavonee 183

1. Chemical Properties 183

A. Karanjin 183

B. LanoeolatinB 185

C. Pongapin 186

D. Kanjone 186

E. Pongaglabrone 188

F. Atanaain 190

G. Gamatin 190

H. Pinnatin 191

IV. Synthetic Furoflavones 193

1. Linear-type 192

2. Angular-type 195

V. References 198

VI. Furoisoflavanoids 301

I. Introduction 201

II. Furoisoflavanones 201

1. Naturally Occurring Furoisoflavanones 201

A. Nepseudin 201

B. Neotenone 218

2. Synthetic Furiosofiavanones 220

A. Angular Furoisoflavones 220

(1) Introduction of a furan nucleus into an isoflavone skeleton (Tanaka’s method) 220

(2) Ethyl orthoformate method (Venkataraman) 224

B. Linear Furo(3', 2'-6,7)isoflavones 226

III. Coumaranochromans 227

1. Introduction 227

2. Naturally Occurring Coumaranochromans 228

A. Homopterocarpin 228

B. Pterocarpin 230

C. Maackiain 233

D. Pisatin 234

E. Neodulin 236

F. Phaseollin 237

IV. Coumaronoflavan-4-ols 238

1. Naturally Occurring Coumaronoflavan-4-ols 238

A. Cyanomaclurin 238

2. Synthetio 11H-benzofuro(3,2-b)-l-benzopyran-11-ones 242

V. Coumaronocoumarins 243

1. Naturally Occurring Coumaronocoumarins 243

A. Coumestrol 243

B. Wedelolactone 246

C. Trifoliol 251

D. Medicagol 253

E. Psoralidin 254

VI. 3-Arylfurocoumarins 258

VII. Coumaronofurocoumarins 259

VIII Furo(3,2-c}-l-benzopyran-4-ones 261

IX. Physiological Activity 262

X. References 266

VII. Chromanochromanones (The Rotenoids) 272

I. Introduction 272

II. Nomenclature 272

III. Rotenone 277

1. Isolation 277

2. Physical Properties 277

3. Structure 278

A. Dehydrorotenol 283

B. Rotenol 289

4. Isomerization (The Isorotenones) 290

A. Isomeric Carbonyl Derivatives of Rotenone 292

B. Hydrogenation 292

C. Oxidation 293

5. Synthesis 295

6. Stereochemistry 300

A. Optical Activity 300

B. Configuration 301

7. Rotenolones, Rotenolols, Isorotenolones, and Isorotenolols 305

IV. Sumatrol 309

V. Malaccol 312

VI. Elliptone 314

VII. Amorphigenin 318

VIII. Dolineone 321

IX. Pachyrrhizone 322

X. References 324

VIII. Less Common Furopyrone Systems 328

I. Isogalloflavin 328

II. Enmein 330

III. References 335

Author Index 337

Subject Index 357