Details

<p><b>I. Furopyrans and -pyrones 1</b></p> <p>I. Naturally Occurring Furopyrans 2</p> <p>1. Flumericin 2</p> <p>2. Anhydrotetrahydroaucubigenin 9</p> <p>II. Synthetic Furopyrans and-pyrones 11</p> <p>III. References 13</p> <p><b>II. Furocoumarins 14</b></p> <p>I. Isolation 15</p> <p>II. Physical Properties 32</p> <p>III. Nomenclature 35</p> <p>IV. Naturally Occurring Furocoumarins 35</p> <p>1. Structure and Chemical Properties 35</p> <p>A. Angelicin 36</p> <p>B. Psoralen 38</p> <p>C. Bergapten 41</p> <p>D. Bergaptol 44</p> <p>E. Isobergapten 44</p> <p>F. Bergamottin 45</p> <p>G. Xanthotoxin 46</p> <p>H. Xanthotoxol 52</p> <p>I. Isoimperatorin 52</p> <p>J. Oxypeucedanin 52</p> <p>K. Ostruthol 53</p> <p>L. Imperatorin 55</p> <p>M. Alloimperatorin 56</p> <p>N. Heraclenin 56</p> <p>O. Isopimpinellin 56</p> <p>P. PheUopterin 58</p> <p>Q. Byakangelicol 59</p> <p>R. Byakangelicin 61</p> <p>S. Pimpinellin 61</p> <p>T. Sphondin 62</p> <p>U. Halfordin and Isohalfordin 62</p> <p>V. Nodakenetin 65</p> <p>W. Peucedanin 69</p> <p>X. Athamantin 70</p> <p>Y. Discophoridin 72</p> <p>Z. Edultin 73</p> <p>AA. Peulustrin 73</p> <p>BB. Columbianadin and Columbianin 76</p> <p>CC. Archangelioin 77</p> <p>DD. Archangelin 78</p> <p>EE. Pyrocanesein 78</p> <p>FF. 4,5',8-Trimethylpsoralen 79</p> <p>GG. Aflatoxins B and G 79</p> <p>2. Configuration 80</p> <p>3. Biosynthesis 82</p> <p>A. α-(/J'-Hydroxypropyl)dihydrofurans and a-Isopropenyl-dihydrofurans 83</p> <p>B. α-IsopropyljS-hydroxyfurans and Relations 84</p> <p>C. Simple Furans 86</p> <p>4. Physiological Activity 87</p> <p>V. References 90</p> <p><b>III. Furochromones 102</b></p> <p>I. Isolation 102</p> <p>II. Physical Properties 103</p> <p>III. Nomenclature 104</p> <p>IV. Naturally Occurring Furochromones 104</p> <p>1. Chemical Properties 104</p> <p>A. Khellin 104</p> <p>(1) Synthesis of khellin 107</p> <p>(2) Synthesis of khellin analogs 112</p> <p>(3) Reactions 112</p> <p>B. Visnagin 133</p> <p>(1) Synthesis of visnagin 134</p> <p>(2) Synthesis of visnagin analogs and related transformations 136</p> <p>(3) Reactions 138</p> <p>C. Khellinol 143</p> <p>D. Khetlinin 144</p> <p>E. Khellol 145</p> <p>F. Ammiol 147</p> <p>G. Visamminol 148</p> <p>2. Color Reactions 150</p> <p>3. Physiological Activity 151</p> <p>V. References 153</p> <p><b>IV. Furoxanthones 160</b></p> <p>I. Naturally Occurring Furoxanthones 160</p> <p>1. Sterigmatocystin 160</p> <p>II. Synthetic Furoxanthones 169</p> <p>III. References 174</p> <p><b>V. Furoflavones 175</b></p> <p>I. Isolation 175</p> <p>II. Physical Properties 175</p> <p>III. Naturally Occurring Furoflavonee 183</p> <p>1. Chemical Properties 183</p> <p>A. Karanjin 183</p> <p>B. LanoeolatinB 185</p> <p>C. Pongapin 186</p> <p>D. Kanjone 186</p> <p>E. Pongaglabrone 188</p> <p>F. Atanaain 190</p> <p>G. Gamatin 190</p> <p>H. Pinnatin 191</p> <p>IV. Synthetic Furoflavones 193</p> <p>1. Linear-type 192</p> <p>2. Angular-type 195</p> <p>V. References 198</p> <p><b>VI. Furoisoflavanoids 301</b></p> <p>I. Introduction 201</p> <p>II. Furoisoflavanones 201</p> <p>1. Naturally Occurring Furoisoflavanones 201</p> <p>A. Nepseudin 201</p> <p>B. Neotenone 218</p> <p>2. Synthetic Furiosofiavanones 220</p> <p>A. Angular Furoisoflavones 220</p> <p>(1) Introduction of a furan nucleus into an isoflavone skeleton (Tanaka’s method) 220</p> <p>(2) Ethyl orthoformate method (Venkataraman) 224</p> <p>B. Linear Furo(3', 2'-6,7)isoflavones 226</p> <p>III. Coumaranochromans 227</p> <p>1. Introduction 227</p> <p>2. Naturally Occurring Coumaranochromans 228</p> <p>A. Homopterocarpin 228</p> <p>B. Pterocarpin 230</p> <p>C. Maackiain 233</p> <p>D. Pisatin 234</p> <p>E. Neodulin 236</p> <p>F. Phaseollin 237</p> <p>IV. Coumaronoflavan-4-ols 238</p> <p>1. Naturally Occurring Coumaronoflavan-4-ols 238</p> <p>A. Cyanomaclurin 238</p> <p>2. Synthetio 11<i>H</i>-benzofuro(3,2-b)-l-benzopyran-11-ones 242</p> <p>V. Coumaronocoumarins 243</p> <p>1. Naturally Occurring Coumaronocoumarins 243</p> <p>A. Coumestrol 243</p> <p>B. Wedelolactone 246</p> <p>C. Trifoliol 251</p> <p>D. Medicagol 253</p> <p>E. Psoralidin 254</p> <p>VI. 3-Arylfurocoumarins 258</p> <p>VII. Coumaronofurocoumarins 259</p> <p>VIII Furo(3,2-c}-l-benzopyran-4-ones 261</p> <p>IX. Physiological Activity 262</p> <p>X. References 266</p> <p><b>VII. Chromanochromanones (The Rotenoids) 272</b></p> <p>I. Introduction 272</p> <p>II. Nomenclature 272</p> <p>III. Rotenone 277</p> <p>1. Isolation 277</p> <p>2. Physical Properties 277</p> <p>3. Structure 278</p> <p>A. Dehydrorotenol 283</p> <p>B. Rotenol 289</p> <p>4. Isomerization (The Isorotenones) 290</p> <p>A. Isomeric Carbonyl Derivatives of Rotenone 292</p> <p>B. Hydrogenation 292</p> <p>C. Oxidation 293</p> <p>5. Synthesis 295</p> <p>6. Stereochemistry 300</p> <p>A. Optical Activity 300</p> <p>B. Configuration 301</p> <p>7. Rotenolones, Rotenolols, Isorotenolones, and Isorotenolols 305</p> <p>IV. Sumatrol 309</p> <p>V. Malaccol 312</p> <p>VI. Elliptone 314</p> <p>VII. Amorphigenin 318</p> <p>VIII. Dolineone 321</p> <p>IX. Pachyrrhizone 322</p> <p>X. References 324</p> <p><b>VIII. Less Common Furopyrone Systems 328</b></p> <p>I. Isogalloflavin 328</p> <p>II. Enmein 330</p> <p>III. References 335</p> <p>Author Index 337</p> <p>Subject Index 357</p>

<p><b>Ahmed Mustafa</b> is the editor of <i>The Chemistry of Heterocyclic Compounds</i>, Volume 23: Furopyrans and Furopyrones, published by Wiley.</p>

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