Synthesis of a Capillarisin Sulfur-Analogue Possessing Aldose Reductase Inhibitory Activity by Selective Isopropylation

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We describe the synthesis of 2-[(4-hydroxyphenyl)thio]-7-isopropoxy-5, 6-dimethoxy-4H-chromen-4-one 2 from 3, 4, 5-trimethoxyphenol 6 via the key intermediate, 3-iodo-7-isopropoxy-5, 6-dimethoxy-4H-chromen-4-one 3. An important feature of this synthetic scheme involves selective alkylation, which can be achieved by two different routes. One route involves the selective isopropylation of a triacetate derivative 4 under basic conditions. The second route employs the selective demethylation of a trimethoxy derivative 5 under acidic conditions followed by isopropylation. The product of these alternative routes, compound 3, is then converted to a capillarisin sulfur analogue 2 in a one-pot reaction via the imidazolyl intermediate 22.
社団法人日本薬学会の論文
2005-09-01