Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 18, Pages 12872-12885Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01523
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Funding
- AlJalila Foundation [AJF202058]
- University of Sharjah [1801110125P]
- American University of Sharjah [BBRI-AS0215]
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The indolo[2,3-a]quinolizines, canthines, and arborescidines natural products show a wide range of bioactivities, with the development of the Complexity-to-Diversity (CtD) strategy providing a powerful tool to transform natural products into various structural and stereochemical diversity. However, limitations in reactions due to functional groups in starting materials still restrict the desired diversity in some transformations.
The indolo[2,3-a]quinolizines, canthines, and arborescidines natural products exhibit a wide range of bioactivities including anticancer, antiviral, antibacterial, and anti-inflammatory, among others. Therefore, the development of modular and efficient strategies to access the core scaffolds of these classes of natural products is a remarkable achievement. The Complexity-to-Diversity (CtD) strategy has become a powerful tool that transforms natural products into skeletal and stereochemical diversity. However, many of the reactions that could be utilized in this process are limited by the type of functional groups present in the starting material, which restrict transformations into a variety of products to achieve the desired diversity. In the course of employing a (CtD) strategy en route to the synthesis of nature-inspired compounds, unexpected stereoelectronic-driven rearrangement reactions have been discovered. These reactions provided a rapid access to indolo[2,3-a] quinolizines-, canthines-, and arborescidines-inspired alkaloids in a modular and diastereoselective manner. The disclosed strategies will be widely applicable to other late-stage natural product transformation programs and drug discovery initiatives.
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