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Short Paper | Regular issue | Vol 87, No. 2, 2013, pp.423-428
Published online, 21st December, 2012
DOI: 10.3987/COM-12-12636
A Practical Synthesis of a Hydroxylated Sesquiterpene Coumarin 10’R-Acetoxy-11’-hydroxyumbelliprenin by Regioselective Dihydroxylation

Yasunao Hattori, Genki Kinami, Kenta Teruya, Kazuto Nosaka, Kazuya Kobayashi, and Kenichi Akaji*

*Department of Medicinal Chemistry, Pharmacetuical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan


A practical synthesis of 10’R-acetoxy-11’-hydroxyumbelliprenin was achieved using regioselective Sharpless asymmetric dihydroxylation as a key reaction, in which the regioselectivity was achieved by using (DHQD)2AQN as a ligand instead of the conventional (DHQD)2PHAL. 10’R-Acetoxy-11’-hydroxyumbelliprenin was synthesized by the coupling of a coumarin unit (umbelliferone) and sesquiterpene unit in 11% overall yield through 5 steps.