By Ahmed Mustafa
Chapter I Furopyrans and ?Pyrones (pages 1–13):
Chapter II Furocoumarins (pages 14–101):
Chapter III Furochromones (pages 102–159):
Chapter IV Furoxanthones (pages 160–174):
Chapter V Furoflavones (pages 175–200):
Chapter VI The Furoisoflavanoids (pages 201–271):
Chapter VII Chromanochromanones (The Rotenoids) (pages 272–327):
Chapter VIII much less universal Furopyrone structures (pages 328–335):
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Additional info for Chemistry of Heterocyclic Compounds: Furopyrans and Furopyrones, Volume 23
Wave ultraviolet light (38566) adapted from Mwejo end Rodighiem,l~(-) indiaeted h t i v i t y ; ( f ) indicated aotivity. 3 A, aaetio soid; n. metone; 0, benzene: D. rwleum ether mixture; E, chloroform; 1. dioxan; Q, ethyl acetate; H, ethyl doohol; I, ethyl croebte- petroleum ether mixture; J, methyl doohol; E. wster; L, benzine; Y, ether; N. butsnol; 0, cyclohexane; P, methylethyl ketone. Natural Source8 and ~urocoumannsConstituents 29 ~~ Natural Some Distribution P&* B F F B. a B B F a Angelica anmnde Angelica archangelk var.
Plant acids are easily separated from furocoumarins by sodium bicarbonate or sodium carbonate solutions. Furocoumarins present in the extracts should be identified before chemical treatment or sublimation' because of the possibility of structural modifications, & consequence of hydrolytic cleavages and thermal lability, resulting in artifacts. 24 Gas-liquid chromatography has been successfully used in the separation of neutral furocoumarins &om Angelica archangelica and Heracleum sibricum, on the other hand, isoprenoid ethers of furocoumarins decomposed at the column temperatures.
The synthesis of 81 wcording to Sp&th’ss7method leads to a mixture of 81and 32and is ambiguous. Robertson and coworkers88have described the methyl ether of an unequivocal synthesie of allobergapten (W), 32. The phenoxy ester (40)was cyclized with sodium ethoxide to yield ethyl 6-benzyloxy-4-methoxycoumarone-2-carboxylate(41, R = CH,C,&) which waa debenzylated with hydrogen and palladium (41, catalyst to ethyl 6-hydroxy-4-methoxycoumarone-2-carboxylate R = H). Application of the Gattermann aldehyde synthesis of the latter substance gave the aldehyde 42, which when decarboxylated gave 7-formy1-6-hydroxy-4-methoxycoumarin (43).
Chemistry of Heterocyclic Compounds: Furopyrans and Furopyrones, Volume 23 by Ahmed Mustafa