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Microgrewiapine C: Asymmetric Synthesis, Spectroscopic Data, and Configuration Assignment
Stephen G Davies1, Ai M Fletcher1, Paul M Roberts1
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.
Journal of Natural Products
|June 30, 2022
Summary
The first asymmetric synthesis of microgrewiapine C, a piperidine alkaloid from Microcos paniculata, has been achieved. This synthesis confirmed the alkaloid's structure and corrected its NMR data, aiding further phytochemical research.
Area of Science:
- Natural Product Chemistry
- Organic Synthesis
- Medicinal Chemistry
Background:
- Microgrewiapine C is a piperidine alkaloid found in Microcos paniculata.
- Its structure and stereochemistry were previously not fully confirmed.
- Accurate structural data is crucial for understanding its biological activity.
Purpose of the Study:
- To report the first asymmetric synthesis of microgrewiapine C.
- To confirm the structure and relative configuration of the natural product.
- To provide corrected spectroscopic data for microgrewiapine C.
Main Methods:
- Asymmetric synthesis of microgrewiapine C.
- Reanalysis of original 1H and 13C NMR spectra.
- Comparison of spectroscopic data between synthetic and natural samples.
Main Results:
- Successful first asymmetric synthesis of microgrewiapine C.
- Correction of 1H and 13C NMR data for the natural product.
- Confirmation of the structure and relative configuration of microgrewiapine C.
- Assignment of the (1R,2S,3S,6S) absolute configuration.
Conclusions:
- The synthesis unequivocally confirms the structure of microgrewiapine C.
- Corrected NMR data are now available for the natural alkaloid.
- Further phytochemical studies are suggested due to potential biosynthetic links.
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