Total Synthesis of the Norhasubanan Alkaloid Stephadiamine

Nina Hartrampf, Nils Winter, Gabriele Pupo, Brian M. Stoltz, Dirk Trauner

Research output: Contribution to journalArticlepeer-review


(+)-Stephadiamine is an unusual alkaloid isolated from the vine Stephania japonica. It features a norhasubanan skeleton, and contains two adjacent α-tertiary amines, which renders it an attractive synthetic target. Here, we present the first total synthesis of stephadiamine, which hinges on an efficient cascade reaction to implement the aza[4.3.3]propellane core of the alkaloid. The α-aminolactone moiety in a highly hindered position was installed via Tollens reaction and Curtius rearrangement. Useful building blocks for the asymmetric synthesis of morphine and (nor)hasubanan alkaloids are introduced.

Original languageEnglish (US)
Pages (from-to)8675-8680
Number of pages6
JournalJournal of the American Chemical Society
Issue number28
StatePublished - Jul 18 2018

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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