Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Total Synthesis of Daphneticin, a Coumarinolignoid
HITOSHI TANAKAICHIRO KATOKAZUO ITO
Author information
Keywords: antitumor
JOURNAL FREE ACCESS

1986 Volume 34 Issue 2 Pages 628-632

Details
Abstract

Daphnetin (3) was transformed with excess benzyl chloride into 7, 8-dibenzyloxycoumarin (4), which on treatment with trifluoroacetic acid in benzene or aluminum chloride in benzene gave 8-benzyloxy-7-hydroxycoumarin (5) in good yield. Condensation of 5 and ethyl 2-bromo-3-(4-acetoxy-3, 5-dimethoxyphenyl)-3-oxopropionate (9), prepared from ethyl benzylsyringoylacetate (7) in two steps, in the presence of sodium hydride afforded 10 in good yield, and the condensation product (10) was then reduced with lithium borohydride to yield a mixture of the diols (11a, b). Treatment of the diols with 36% hydrochloric acid in acetic acid provided daphneticin (1) in 68% yield.

Content from these authors
© The Pharmaceutical Society of Japan
Previous article Next article
feedback
Top