ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
2 files

Asymmetric Total Synthesis of Arcutinidine and Arcutinine

preprint
submitted on 30.05.2019, 03:49 and posted on 30.05.2019, 15:37 by Shupeng Zhou, Kaifu Xia, Ang Li
We have accomplished the asymmetric total synthesis of arcutinidine and arcutinine, two arcutine-type C20-diterpenoid alkaloids. A pentacyclic intermediate was rapidly assembled by using two Diels−Alder reactions. A cascade sequence of Prins cyclization and Wagner−Meerwein rearrangement was then developed to construct the core of arcutinidine, which was further elaborated into an oxygenated pentacycle through a scalable route. Chemoselective reductive amination followed by spontaneous imine formation furnished the pyrroline motif at a final stage.

History

Email Address of Submitting Author

ali@sioc.ac.cn

Institution

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

Country

China

ORCID For Submitting Author

0000-0002-8808-0636

Declaration of Conflict of Interest

The authors declare no conflict of interest.

Exports