Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.