V. Gujral, S. Gupta
Dec 1, 1979
Citations
0
Influential Citations
6
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
1,3,5-Trihydroxyxanthen-9-one reacts with 2-methylbut-3-en-2-ol in presence of a catalytic amount of BF3-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 (3), in good yield, and 1,3,5-trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one (4) in poor yield. Compounds 3 and 4, 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 3 and 4 on oxidative cyclisation with DDQ, gave 6-desoxyisojacareubin and 6-desoxyjacareubin respectively, completely identical with authentic natural samples.