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Updated: Jul 5, 2026

Applications of Liquid-Chromatography Tandem Mass Spectrometry in Natural Products Research: Tropane Alkaloids as a Case Study
Published on: March 8, 2024
Total synthesis of the Securinega alkaloid (-)-secu'amamine A
Peng Liu1, Sungwoo Hong, Steven M Weinreb
1Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Abstract:
The first enantioselective total synthesis of the rearranged Securinega alkaloid (-)-secu'amamine A is reported starting from D-proline as the source of absolute chirality. The synthesis requires 15 steps starting from D-proline-derived N-trityl aldehyde 11 and proceeds in approximately 9% overall yield. Key steps include a stereoselective conjugate addition of pyrrolidino enedione 19 to afford indolizidine 24 as the major product and cyclization/lactonization of diketoester 25 to produce tetracycle 26. In addition, 1H NMR NOE studies and X-ray analysis on the synthetic alkaloid have established that the indolizidine moiety is trans-fused.
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