Syntheses of Ring-substituted Flavonoids and Allied Compounds. XI. Synthesis of Hinokiflavone

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概要

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• Permethylated 3-nitrobisflavonyl ether (XXIV), the key-intermediate for the synthesis of the proposed structure (XXX), was prepared by the condensation of 8-hydroxy-4', 5,7-trimethoxyflavone (XX) with 4'-iodo-3'-nitro-5,7-dimethoxyflavone (XXIII) in DMSO in the presence of K_2CO_3 at 110°for 1 hr. The nitro ether was reduced by Na_2S_2O_4 in aq. DMF, diazotized and decomposed with 50% H_3PO_2 to give XXVII, which proved to be different from pentamethyl ether of natural hinokiflavone. An alternative bisflavone with 4', 6''-coupling positions has now been synthesized in a similar route described above. XXXIV was condensed with XXIII to 3'-nitro ether (XXXV), which was reduced, diazotized and decomposed to give permethylated ether (XXXVIII), identical with permethyl ether of natural hinokiflavone. The synthesized methyl ether was finally demethylated by means of HI・Ac_2Oat 130-140° for 3 hr to give 4''', 5,5'', 7,7'-pentahydroxy-4', 6''-bisflavonyl ether (XLII) identical with natural hinokiflavone. 4', 8''-Bisflavone (XXVII) was converted into a bisflavone (XLII) identical with natural hinokiflavone, when heated with HI・Ac_2O as above (Wessely-Moser rearrangement).

• 公益社団法人日本薬学会の論文
• 1968-12-25

著者

• 中沢 浩一

  Sanwa Kagaku Kenkyusho Co. Ltd.

• 中沢 浩一

  Gifu College of Pharmacy

関連論文

• Syntheses of Ring-substituted Flavonoids and Allied Compounds. XII. Synthesis of (±)-Fukugetin Heptamethyl Ether
• Synthesis of (±)-Fukugetin Heptamethyl Ether
• Syntheses of Ring-substituted Flavonoids and Allied Compounds. X. Synthesis of Ginkgetin.
• Syntheses of Ring-substituted Flavonoids and Allied Compounds. XI. Synthesis of Hinokiflavone
• Syntheses of Nuclear-substituted Flavonoids and Allied Compounds. IX. Syntheses of Tetramethyl Ether and Dimethyl Ether of Ginkgetin.
• Synthesis of Ginkgetin Tetramethyl Ether

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