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Short Paper | Special issue | Vol 90, No. 1, 2015, pp.659-672
Published online, 3rd June, 2014
DOI: 10.3987/COM-14-S(K)23
N-(2,3,4,5,6-Pentafluorophenyl)maleimide as a Powerful Dienophile in Dearomatizing Diels-Alder Reactions

Koichi Hagiwara, Masafumi Iwatsu, Daisuke Urabe, and Masayuki Inoue*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan


Here we demonstrate that N-(2,3,4,5,6-pentafluorophenyl)maleimide effectively promotes dearomatizing Diels-Alder reactions of 2,5-dimethylbenzene-1,4-diol and naphthalen-2-ol derivatives. The present reactions successfully converted the sp2-rich components to the desired products with multiple sp3-carbons in a single step. The adduct was further derivatized into the intermediate for our synthesis of 9-demethyl-10,15-dideoxyryanodol, an analogue of a sp3-rich natural product, in two steps.