@article{7a1aed40bcd645529fb5ad991a8bad2b,
title = "Total Synthesis of the Norhasubanan Alkaloid Stephadiamine",
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.",
author = "Nina Hartrampf and Nils Winter and Gabriele Pupo and Stoltz, {Brian M.} and Dirk Trauner",
note = "Funding Information: 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 Ren{\'e} 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 LMUMentoring program (fellowship N.H.), the Otto Bayer Scholarship (fellowship to N.H.) as well as the Deutsche Forschungsge-meinschaft (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. Funding Information: Additionally we acknowledge the Deutsche Telekom Foundation (Ph.D. fellowship to N.H.), the LMUMentoring 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. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",
year = "2018",
month = jul,
day = "18",
doi = "10.1021/jacs.8b01918",
language = "English (US)",
volume = "140",
pages = "8675--8680",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "28",
}