CONSTITUTION AND SYNTHESIS OF NORANHYDROICARITIN AND ISOANHYDROICARITIN

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Kaempferol (1) when reacted with 2-hydroxy-2-methyl-3-butene in the presence of borontrifluoride etherate yielded a mixture of 6,8-di-(3-methylbut-2-enyl) derivative (2), 4″, 5″-dihydro-6″, 6″-dimethyl pyrano (2″,3″ : 7,8)-kaempferol (3) and 8-(3-methylbut-2-enyl) derivative (4). The orientation of alkenyl unit in compound 4 has been unambiguously established and then it agrees in direct comparison with natural noranhydroicaritin. 1Complete acetylation of 4, followed by reaction of 5 with one mole of methyl iodide in the presence of dry K2CO3 and acetone afforded 8-(3-methylbut-2-enyl)-rhamnocitrin triacetate (6) which on deacetylation finally gave natural isoanhydroicaritin 1(7).

Journal

  • Chemistry Letters

    Chemistry Letters 3 (9), 1025-1028, 1974-09-05

    The Chemical Society of Japan

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