Furopyrans and Furopyrones, Volume 23

Ahmed Mustafa, Chemistry Department, Cairo University.

• I. Furopyrans and -pyrones 1I. Naturally Occurring Furopyrans 21. Flumericin 22. Anhydrotetrahydroaucubigenin 9II. Synthetic Furopyrans and-pyrones 11III. References 13II. Furocoumarins 14I. Isolation 15II. Physical Properties 32III. Nomenclature 35IV. Naturally Occurring Furocoumarins 351. Structure and Chemical Properties 35A. Angelicin 36B. Psoralen 38C. Bergapten 41D. Bergaptol 44E. Isobergapten 44F. Bergamottin 45G. Xanthotoxin 46H. Xanthotoxol 52I. Isoimperatorin 52J. Oxypeucedanin 52K. Ostruthol 53L. Imperatorin 55M. Alloimperatorin 56N. Heraclenin 56O. Isopimpinellin 56P. PheUopterin 58Q. Byakangelicol 59R. Byakangelicin 61S. Pimpinellin 61T. Sphondin 62U. Halfordin and Isohalfordin 62V. Nodakenetin 65W. Peucedanin 69X. Athamantin 70Y. Discophoridin 72Z. Edultin 73AA. Peulustrin 73BB. Columbianadin and Columbianin 76CC. Archangelioin 77DD. Archangelin 78EE. Pyrocanesein 78FF. 4,5',8-Trimethylpsoralen 79GG. Aflatoxins B and G 792. Configuration 803. Biosynthesis 82A. α-(/J'-Hydroxypropyl)dihydrofurans and a-Isopropenyl-dihydrofurans 83B. α-IsopropyljS-hydroxyfurans and Relations 84C. Simple Furans 864. Physiological Activity 87V. References 90III. Furochromones 102I. Isolation 102II. Physical Properties 103III. Nomenclature 104IV. Naturally Occurring Furochromones 1041. Chemical Properties 104A. Khellin 104(1) Synthesis of khellin 107(2) Synthesis of khellin analogs 112(3) Reactions 112B. Visnagin 133(1) Synthesis of visnagin 134(2) Synthesis of visnagin analogs and related transformations 136(3) Reactions 138C. Khellinol 143D. Khetlinin 144E. Khellol 145F. Ammiol 147G. Visamminol 1482. Color Reactions 1503. Physiological Activity 151V. References 153IV. Furoxanthones 160I. Naturally Occurring Furoxanthones 1601. Sterigmatocystin 160II. Synthetic Furoxanthones 169III. References 174V. Furoflavones 175I. Isolation 175II. Physical Properties 175III. Naturally Occurring Furoflavonee 1831. Chemical Properties 183A. Karanjin 183B. LanoeolatinB 185C. Pongapin 186D. Kanjone 186E. Pongaglabrone 188F. Atanaain 190G. Gamatin 190H. Pinnatin 191IV. Synthetic Furoflavones 1931. Linear-type 1922. Angular-type 195V. References 198VI. Furoisoflavanoids 301I. Introduction 201II. Furoisoflavanones 2011. Naturally Occurring Furoisoflavanones 201A. Nepseudin 201B. Neotenone 2182. Synthetic Furiosofiavanones 220A. Angular Furoisoflavones 220(1) Introduction of a furan nucleus into an isoflavone skeleton (Tanaka's method) 220(2) Ethyl orthoformate method (Venkataraman) 224B. Linear Furo(3', 2'-6,7)isoflavones 226III. Coumaranochromans 2271. Introduction 2272. Naturally Occurring Coumaranochromans 228A. Homopterocarpin 228B. Pterocarpin 230C. Maackiain 233D. Pisatin 234E. Neodulin 236F. Phaseollin 237IV. Coumaronoflavan-4-ols 2381. Naturally Occurring Coumaronoflavan-4-ols 238A. Cyanomaclurin 2382. Synthetio 11H-benzofuro(3,2-b)-l-benzopyran-11-ones 242V. Coumaronocoumarins 2431. Naturally Occurring Coumaronocoumarins 243A. Coumestrol 243B. Wedelolactone 246C. Trifoliol 251D. Medicagol 253E. Psoralidin 254VI. 3-Arylfurocoumarins 258VII. Coumaronofurocoumarins 259VIII Furo(3,2-c}-l-benzopyran-4-ones 261IX. Physiological Activity 262X. References 266VII. Chromanochromanones (The Rotenoids) 272I. Introduction 272II. Nomenclature 272III. Rotenone 2771. Isolation 2772. Physical Properties 2773. Structure 278A. Dehydrorotenol 283B. Rotenol 2894. Isomerization (The Isorotenones) 290A. Isomeric Carbonyl Derivatives of Rotenone 292B. Hydrogenation 292C. Oxidation 2935. Synthesis 2956. Stereochemistry 300A. Optical Activity 300B. Configuration 3017. Rotenolones, Rotenolols, Isorotenolones, and Isorotenolols 305IV. Sumatrol 309V. Malaccol 312VI. Elliptone 314VII. Amorphigenin 318VIII. Dolineone 321IX. Pachyrrhizone 322X. References 324VIII. Less Common Furopyrone Systems 328I. Isogalloflavin 328II. Enmein 330III. References 335Author Index 337Subject Index 357