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Short Paper | Regular issue | Vol 89, No. 9, 2014, pp.2161-2167
Published online, 8th August, 2014
DOI: 10.3987/COM-14-13053
Microwave-Aided One-Pot Dehydration of the Alcohol Derived from (−)-Shikimic Acid for Efficient Synthesis of Pericosines

Koji Mizuki, Yusuke Yoneshige, Rikiya Kawahata, Hiroki Yoneyama, Shinya Harusawa, and Yoshihide Usami*

*Laboratory of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan

Abstract

Dehydrating conditions of shikimate-derived alcohol 7, an early intermediate in the synthesis of the pericosine family of marine natural products, were examined. The triflate 8 was effectively converted to cyclohexadiene 9 with excess 4-N,N-dimethylaminopyridine (DMAP) at room temperature for 24 h. The reaction time was dramatically shortened by heating under microwave (MW) irradiation, preventing formation of the Diels–Alder type byproduct 14. Furthermore, the MW-aided one-pot dehydration of alcohol 7 with Tf2O and DMAP (2.4 eq.) to form diene 9 was realized.