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Report | Regular issue | Vol 23, No. 8, 1985, pp.1991-1997
Published online, 1st January, 1970
DOI: 10.3987/R-1985-08-1991
Total Synthesis of Cleomiscosin B, a Coumarinolignoid

Hitoshi Tanaka, Ichiro Kato, and Kazuo Ito*

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan

Abstract

Direct alkylation of fraxetin (3) with ethyl 2-bromo-3-(4-benzyoxy-3-methoxyphenyl)-3-oxopropionate (4) by utilizing about 1 equivalent of sodium hydride afforded the desired compound (6) as the major product, which was reduced with lithium borohydride in tetrahydrofuran to give the threo and erythro isomers (7a,b). The isomers underwent cyclization reaction with 5% sulfuric acid and subsequent hydrolysis of the cyclization product (10) furnished cleomiscosin B (1).