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DOI: 10.1055/s-0041-1737276
Total Synthesis of (–)-Aristoquinoline via an Intramolecular Nitrilium Ion Cyclization
Funding for this project was provided by the Fisher College of Science and Mathematics (Towson University) through an undergraduate research grant. This work was also supported by instrumentation provided through the National Science Foundation under Grant Nos. 0923051 and 1531562.
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Abstract
The enantioselective total synthesis of the alkaloid aristoquinoline has been achieved in seven steps and 26% overall yield. A new preparation of the useful synthetic building block (–)-α-terpinyl amine was also developed in order to avoid stoichiometric mercury reagents or azide-containing intermediates. Key steps in the optimized synthetic route include an intramolecular nitrilium ion cyclization to form the characteristic azabicyclo[3.3.1]nonane ring system and a diastereoselective reduction of the resulting imine mixture to afford the natural product. An isomer of aristoquinoline containing an exocyclic alkene was also obtained and found to exhibit unusual chromatographic and spectroscopic properties.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737276.
- Supporting Information
Publication History
Received: 03 September 2021
Accepted after revision: 03 October 2021
Article published online:
22 November 2021
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