Synthesis of irigenin and of tectorigenin, derivatives of 5,7-dihydroxy-6-methoxyisoflavone
β Scribed by W. Baker; D.F. Downing; A.J. Floyd; B. Gilbert; W.D. Ollis; R.C. Russell
- Publisher
- Elsevier Science
- Year
- 1960
- Tongue
- French
- Weight
- 201 KB
- Volume
- 1
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
OF the twenty-one known natural isoflavones,' three, tectorigenin, irigenin, and caviunin, are derivatives of 5,7-dihydroxy-6-methoqyisoflevone. This particular orientation of substituents makes a direct synthesis difficult, but a method, which we believe to be general, for the synthesis of such isoflavones is now described in the cases of tectorigenin and irigenin. Tectorigenin has previously been synthesised, 2 but it is of interest to note that irigenin, although it ' ?i. K. :;'o.rburton Quart. Rev. & 67 (1954). K. Venkataraman~ Fortschritte der Chem. Org. Nat. I& 1 ( 1959).
π SIMILAR VOLUMES
The above mentioned compounds have been prepared by methods involving isomeric change from the more readily available 5,7,&substituted isoflavones.
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So far one has only succeded in synthetising 5.7~dihydroxy-6-methoxyflavonea bearing not more than one substituent on the phenyl side Aain /B-ring/ l-9. b tried to solve this problem by alkaline ring isomerization 10-12.