Total Synthesis of the Norhasubanan Alkaloid Stephadiamine

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

Research output: Contribution to journalArticle

Abstract

(+)-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
Volume140
Issue number28
DOIs
StatePublished - Jul 18 2018

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Total Synthesis of the Norhasubanan Alkaloid Stephadiamine'. Together they form a unique fingerprint.

  • Cite this

    Hartrampf, N., Winter, N., Pupo, G., Stoltz, B. M., & Trauner, D. (2018). Total Synthesis of the Norhasubanan Alkaloid Stephadiamine. Journal of the American Chemical Society, 140(28), 8675-8680. https://doi.org/10.1021/jacs.8b01918