Formal Synthesis of Phomactin A via the PrinsConia-ene Cascade Cyclization Approach

来源 :第五届岭南有机化学论坛暨华南理工大学-兰州大学有机化学双边论坛 | 被引量 : 0次 | 上传用户:zhoushucheng0533
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Phomactin A is a marine natural product isolated from marine fungus Phoma sp.in 1991 which bears a tricyclic furnochromanskeleton integrated into a 12-membered macrocycle with six stereogenic centers including one all-carbon quaternary stereogenic center.In addition to its unique structural features,this natural product is found to be a selective antagonist of platelet activating factor(PAF).Base on our retrosynthetic analysis(Scheme 1),we envisioned that the 1-oxadecalin core of Phomactin A can be constructed through the Prins/Conia-ene cyclization cascade approach(which was developed by our group),and the C ring of the tricyclic furnochromanskeleton can be established via a late stage γ-hydroxylation approach.Finally,Suzuki cross coupling could be used to install the 12-membered ring and accomplished the total synthesis of Phomactin A according to the literaure procedures.
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