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Note | Special issue | Vol 77, No. 1, 2009, pp.603-610
Published online, 18th August, 2008
DOI: 10.3987/COM-08-S(F)29
Dihydroxylation of Functionalized Coumarin Derivatives

Keiko Fusegi, Takuya Kumamoto,* Waka Nakanishi, and Tsutomu Ishikawa*

*Graduate School of Pharmaceutical Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

7-Acetoxy- and 7-tosyloxycoumarins were successfully dihydroxylated in RuCl3/NaIO4/CeCl3 system to give the corresponding glycol derivatives in excellent yields. Tricyclic coumarin with tetrasubstituted olefin function also gave the desired diol in good yield. Introduction of electron-deficient protecting group to coumarin skeleton is critical for the successful dihydroxylation.