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Published July 18, 2018 | Accepted Version + Supplemental Material
Journal Article Open

Total Synthesis of the Norhasubanan Alkaloid Stephadiamine


(+)-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.

Additional Information

© 2018 American Chemical Society. Received: February 15, 2018; Published: June 11, 2018. We acknowledge Dr. Anastasia Hager and Dr. Dominik Hager for their contributions in the early stages of this project. The authors thank Dr. Hong-Dong Hao and Dr. Julius R. Reyes for experimental assistance, Dr. Scott Virgil and René Rahimoff for assistance with HPLC, and Dr. Peter Mayer for X-ray structure analysis. Additionally, we acknowledge the Deutsche Telekom Foundation (Ph.D. fellowship to N.H.), the LMU Mentoring program (fellowship N.H.), the Otto Bayer Scholarship (fellowship to N.H.) as well as the Deutsche Forschungsgemeinschaft (SFB 749 and CIPSM) for generous funding. B.M.S. thanks the NIH-NIGMS (R01GM080269) for partial financial support of this project. Dr. Felix Hartrampf and Dr. Julius R. Reyes are acknowledged for excellent support in the course of this project and with the preparation of this paper. The authors declare no competing financial interest.

Attached Files

Accepted Version - nihms-985447.pdf

Supplemental Material - ja8b01918_si_001.pdf

Supplemental Material - ja8b01918_si_002.cif


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August 19, 2023
October 18, 2023