Li Shao
1997
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Journal
Chemical Research in Chinese Universities
Abstract
3-Butylidene-5-hydroxyphthalide (1), isolated from Ligusticum wallichii., hasbeen first syntheslzed starting from 4-hydroxybenzoic acid in 8 steps. Herein compound 4 ondirected matallation with n-butyllithium in the presence of TMEDA followed by treatmentwith DMF gave 5 in 80% yield. The hydrolysis of 5 by employing 4 mol HCl aq. gave 6 in83% yield. Compound 6 was converted to the acid (7) by the conventional method. Com-pound 7 was dissolved in sodium bicarbonate and reacted with a solution of iodine in aqueouspotassium iodide to give 8. Iodophthalide (8) was reacted with sodium acetate in refluxingethanol to furnish 9 in 94% yield- Demethylation of 9 was conducted in methylene chloridewith boron tribromide to give the title compound(1). The spectral data of 1 are consistentwith those of the natural product.