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Synthesis of Phantasmidine

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Figshare2016-02-23 更新2026-04-29 收录
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https://figshare.com/articles/dataset/Synthesis_of_Phantasmidine/2694586
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Reaction of 6-chloro-2-fluoro-3-pyridineacetamide with 1,2-bis(trimethylsilyloxy)cyclobutene in ether saturated with hydrogen chloride afforded the keto amide in 85% yield. In the key step, treatment of the keto amide with aqueous KOH in t-BuOH resulted in a tandem intramolecular aldol reaction−intramolecular nucleophilic aromatic substitution sequence to give the tetracylic lactam in 46% yield. Reduction of the lactam with BH3 in THF gave phantasmidine in 67% yield.
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2016-02-23
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