First stereoselective total synthesis and anticancer activity of new amide alkaloids of roots of pepper

The first stereoselective total synthesis of new natural amide alkaloids 1–3 have been achieved from commercially available starting materials. Wittig olefination, Sharpless asymmetric dihydroxylation, epoxidation, a trans regioselective opening of 2,3-epoxy alcohol, Horner–Wadsworth–Emmons (HWE) olefination and amide coupling are the key steps. The amide alkaloids 1–3 are evaluated for their anticancer activity against colon (HT-29), breast (MCF-7) and lung (A-549) human cancer cell lines for the first time.

Graphical abstractThe first stereoselective total synthesis of new natural amide alkaloids 1–3 and their anti cancer activity is reported.Figure optionsDownload full-size imageDownload as PowerPoint slide