Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Org Lett. 2011 Feb 4;13(3):526-9. doi: 10.1021/ol102929m. Epub 2010 Dec 22.
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 BH(3) in THF gave phantasmidine in 67% yield.
6-氯-2-氟-3-吡啶乙酰胺与 1,2-双(三甲基甲硅烷氧基)环丁烯在氯化氢饱和的乙醚中的反应以 85%的收率得到酮酰胺。在关键步骤中，用氢氧化钾的叔丁醇溶液处理酮酰胺，导致串联的分子内羟醛反应-分子内亲核芳香取代序列，以 46%的收率得到四元环内酰胺。用硼氢化硼在四氢呋喃中还原内酰胺得到幻太定，收率为 67%。
