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Short Paper | Special issue | Vol 90, No. 1, 2015, pp.706-714
Published online, 17th July, 2014
DOI: 10.3987/COM-14-S(K)40
Synthetic Study of Afritoxinone A: Stereoselective Construction of Furopyranone Moiety

Hideki Abe, Toshihiro Yoshie, Takumi Wagatsuma, Toyoharu Kobayashi, and Hisanaka Ito*

*School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Stereoselective construction of the furopyranone moiety of the natural product afritoxinone A was demonstrated. This synthetic methodology features (i) stereoselective 1,4-addition of a tricyclic ring system, (ii) oxidative cleavage of the diol, followed by hydration of the resulting dialdehyde group, and (iii) acetalization via cationic cyclization of the pyranediol with the tert-butyl ester tether.