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A novel approach for the synthesis of lophocladines A, B and C1 analogues
- Disadee, Wannaporn, Ploypradith, Poonsakdi, Aree, Thammarat, Chaichit, Narongsak, Ruchirawat, Somsak
- Tetrahedron letters 2011 v.52 no.46 pp. 6142-6144
- amines, chemical structure, cytotoxicity, leukemia, oxidation
- A novel approach for the syntheses of lophocladines A and B has been developed. These compounds were prepared in 4–6 steps with moderate to excellent overall yields. The key step involved the nucleophilic substitution of 4-chloronicotinic acid with the carbanion generated from phenylacetonitrile. Subsequent reduction of the cyano group, lactamization and oxidation furnished lophocladine A in 50% yield over 4 steps. Further amination with various amines led to lophocladine B and its C1 analogues in good yields. In addition, the synthesized compounds were evaluated for their cytotoxicity against leukaemia cells.