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These are preliminary reports that have not been peer-reviewed.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
0/0

Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D

preprint
revised on 04.10.2019 and posted on 04.10.2019 by You-Chen Lin, Aubert Ribaucourt, Yasamin Moazami, Joshua Pierce
A concise synthesis of the tricyclic guanidinium alkaloid batzelladine D has been accomplished in a sequence of 8 steps from readily available building blocks. Highlights of the synthesis include gram-scale preparation of a late stage intermediate, pinpoint stereocontrol around the tricyclic skeleton and a modular strategy that enables analog generation. A key bicyclic b-lactam intermediate serves to not only control stereochemistry, but also serves as a pre-activated coupling partner to install the ester sidechain. The stereo-controlled synthesis allowed for the investigation of the antimicrobial activity of batzelladine D, demonstrating promising activity that is more potent for non-natural stereoisomers.

Funding

Synthesis and Chemical Biology of Bioactive Guanidine Alkaloids

National Institute of General Medical Sciences

Find out more...

History

Email Address of Submitting Author

jgpierce@ncsu.edu

Institution

NC State University

Country

United States

ORCID For Submitting Author

0000-0001-9194-3765

Declaration of Conflict of Interest

The authors declare not conflict of interest.

Exports