Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, by Gwynn P. Ellis

By Gwynn P. Ellis

Content material:
Chapter I Chromenes, Chromanones, and Chromones—Introduction (pages 1–10): G. P. Ellis
Chapter II 2H? and 4H?1?Benzopyrans (pages 11–139): E. E. Schweizer and Deborah Meeder?Nycz
Chapter III 3?Chromanols and 4?Chromanols (pages 141–192): I. M. Lockhart
Chapter IV 3?Chromanones (pages 193–206): I. M. Lockhart
Chapter V 4?Chromanones (pages 207–428): I. M. Lockhart
Chapter VI 2,4?Chromandiones and 2,3,4?Chromantriones (pages 429–453): I. M. Lockhart
Chapter VII certainly happening Chromones (pages 455–480): G. P. Ellis
Chapter VIII Analytical facets of Chromones (pages 481–494): G. P. Ellis
Chapter IX common equipment of getting ready Chromones (pages 495–555): G. P. Ellis
Chapter X Chromone and its Benzo Derivatives (pages 557–580): G. P. Ellis
Chapter XI Alkylchromones (pages 581–631): G. P. Ellis
Chapter XII Hydroxychromones (pages 633–689): G. P. Ellis
Chapter XIII Alkoxychromones (pages 691–748): G. P. Ellis
Chapter XIV Halochromones (pages 749–779): G. P. Ellis
Chapter XV Nitrochromones (pages 781–798): G. P. Ellis
Chapter XVI Aminochromones (pages 799–854): G. P. Ellis
Chapter XVII Ketonic Chromones (pages 855–901): G. P. Ellis
Chapter XVIII Chromone Carbonitriles and Tetrazole Derivatives (pages 903–920): G. P. Ellis
Chapter XIX Chromone Carboxaldehydes (pages 921–942): G. P. Ellis
Chapter XX Chromone Carboxylic Acids and Their Derivatives (pages 943–1042): G. P. Ellis
Chapter XXI Bischromones and Bichromones (pages 1043–1083): G. P. Ellis

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Additional resources for Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones, Volume 31

Example text

A preliminary structure ( 5 5 ) was assigned to lapachenole from these results,23 and this was finally verified by synthesis of both lapachenole and its dihydro c o m p o ~ n dz3. Me OQ COzH OH (54) OMe (5 5 ) 38 2H- and 4H-1-Benzopyrans L. ~~ oxidation gave benzaldehyde and P-tubaic acid (59) whose structure was known; lonchocarpin was then syn77 thesized from benzaldehyde and /3-tubaic M . O-Methyalloevodionolg> 24, 58 M e o w ; ; OMe (60) 0-Methylalloevodionol is the methyl ether of alloevodionol and is isolated from milled leaves by extraction and chromatography or by steam distillation of leaves and terminal branchlets.

B). 2H- and 4H-1-Benzopyrans 40 P . Mundulone78 (63) Mundulone is a complex natural product extracted from the bark of a Mundulia sericea tree. From various tests the following data were compiled about its structure: (a) analytically, it was found to contain one methoxyl and one alcoholic hydroxyl group; (b) an infrared peak at 1631 cm-l indicated a conjugated carbonyl which formed all characteristic derivatives for such compounds; (c) a change in ultraviolet spectrum of the natural product after hydrogenation showed one carbon-arbon double bond removed from the main chromophore; (d) mild alkaline fusion of mundulone gave formic acid and a deoxybenzoin, mundulitone (C,,H,,OMe); (e) hydrolysis of the methylated dihydromundulone followed by peroxide oxidation gave two acids, one of which was dihydro-P-tubaic acid methyl ether and the second of unknown structure; v) oxidation of the methyl ether of mundulitone gave P-tubaic acid methyl ether and the same unknown acid found in (e); and ( g ) continued degradation to find the structure of mundulonic acid led to the deduction of the fmal structure of mundulone.

Treatment of the compound (72) with formaldehyde and sulfuric acid gave the dimer (73), identical to the octahydro GMe HO \OH Me (72) OH OH (73) derivative of the natural product. Thus the unhydrogenated product, rottlerone, was also assigned a dimeric form, now consistent with available information. Rottlerone itself was not synthesized because of its instability. Me S . Siccanochromene A (74) and Siccanochromene B (75)54,55,s5386 M e \ w / OH \ Me Me (74) ,’ OH Me Me (75) Four new 2H-1-benzopyrans were isolated in the late 1960s from a culture broth of a pathogenic plant fungus, Helminthosporium siccans Dreschler, of which two were assigned the siccanochromene A and B s t r ~ c t u r e s .

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