Total synthesis of the Securinega alkaloid (-)-secu'amamine A

Peng Liu, Sungwoo Hong, Steven M. Weinreb

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44 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)7562-7563
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number24
DOIs
StatePublished - Jun 18 2008

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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