As a part of structureactivity relationship studies to elucidate structure requirements for eliciting antifungal activity, an artificial analog of amphidinol 3 (AM3) was designed. A truncated analog corresponding to the C21C39/C52C67 section was synthesized by using SuzukiMiyaura coupling and JuliaKocienski olefination as key steps. An expeditious and versatile method to construct the C53C67 polyene section was also developed based on a linchpin strategy via successive cross-coupling reactions. The analog elicited no antifungal activity, suggesting that the two tetrahydropyran rings of AM3 are necessary to elicit antifungal activity.
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