1033699-80-7Relevant academic research and scientific papers
Total synthesis of the Securinega alkaloid (-)-secu'amamine A
Liu, Peng,Hong, Sungwoo,Weinreb, Steven M.
, p. 7562 - 7563 (2008)
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. Copyright
