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Communication | Regular issue | Vol 96, No. 7, 2018, pp.1197-1202
Published online, 22nd June, 2018
DOI: 10.3987/COM-18-13927
Synthesis of an Analog of Amphidinol 3 Corresponding to the C31–C67 Section

Tomoyuki Koge, Yuma Wakamiya, Makoto Ebine, and Tohru Oishi*

*Department of Chemistry, Faculty and Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan

Abstract

An artificial analog corresponding to the C31–C67 section of amphidinol 3 (AM3) was designed as a part of the structure–activity relationship studies to elucidate structure requirements for eliciting antifungal activity. To reduce the number of synthetic steps, the 43-deoxy-51-epi derivative containing common tetrahydropyran ring system was designed and synthesized from a pivotal intermediate in 17 steps. The analog elicited no antifungal activity, suggesting that not only the two tetrahydropyran rings, but also polyol section of AM3 are necessary to elicit antifungal activity.