Synthesis of some 3-methylbut-2-enylated 1,3,5-trihydroxyxanthones.

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概要

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• 1,3,5-Trihydroxyxanthen-9-one reacts with 2-methylbut-3-en-2-ol in presence of a catalytic amount of BF<SUB>3</SUB>-etherate to yield a mixture of 1,3,5-trihydroxy-2,4-bis-(3-methylbut-2-enyl)xanthen-9-one, in poor yield, identical with natural 8-desoxygartanin along with 1,3,5-trihydroxy-4-(3-methylbut-2-enyl)xanthen-9-one (<B>3</B>), in good yield, and 1,3,5-trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one (<B>4</B>) in poor yield. Compounds <B>3</B> and <B>4</B>, the probable biogenetic precursors of 6-desoxyisojacareubin and 6-desoxyjacareubin, have been reported to occur in nature as such but were characterised as their dimethyl ethers. Compounds <B>3</B> and <B>4</B> on oxidative cyclisation with DDQ, gave 6-desoxyisojacareubin and 6-desoxyjacareubin respectively, completely identical with authentic natural samples.

• 公益社団法人 日本化学会の論文

著者

• Gupta S.

  Department Of Agricultural And Food Engineering Indian Institute Of Technology Kharagpur

• Gujral Vinod

  Department of Chemistry, University of Delhi

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