 Amphidinol 3 (AM3) is a polyene-polyhydroxy metabolite isolated from the marine dinoflagellate Amphidinium klebsii. It is a potent membrane-permeabilizing agent and exhibits the strongest antifungal activity in its family along with hemolytic activity. Fascinated by its unique mode of action and complex molecular architecture we developed a novel strategy to construct the C16-C30 fragment of AM3, which utilizes a temporary silicon-tethered ring-closing metathesis reaction sequence (TST-RCM). The highly convergent and efficient union of the C15-30 sulfone with the C1-15 epoxide then completes the synthesis of the polyol fragment. Importantly, this approach confirms the relative configuration of this fragment of the natural product.

Asymmetric synthesis of the C1-C31 fragment of Amphidinol 3

248th National Meeting (2014)

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