First stereoselective total synthesis and anticancer activity of new amide alkaloids of roots of pepper |
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| Authors: | Ch Srinivas ChNS Sai Pavan Kumar B China Raju V Jayathirtha Rao VGM Naidu S Ramakrishna Prakash V Diwan |
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| Institution: | 1. Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad 500 607, India;2. Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 607, India;3. Pharmacology Division, Indian Institute of Chemical Technology, Hyderabad 500 607, India;4. National Institute of Pharmaceutical Education and Research, Balanagar, Hyderabad 500037, India |
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| Abstract: | 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. |
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