Stereoselective Late-Stage Transformations of Indolo[2,3- a ]quinolizines Skeleta to Nature-Inspired Scaffolds.

Autor: Srinivasulu V; Sharjah Institute for Medical Research, University of Sharjah, P.O. Box 27272, Sharjah 00000, UAE., Sieburth SM; Temple University, Department of Chemistry, 201 Beury Hall, Philadelphia, Pennsylvania 19122, United States., Khanfar MA; College of Science, Department of Chemistry, University of Sharjah, P.O. Box 27272, Sharjah 00000, UAE., Abu-Yousef IA; Department of Biology, Chemistry and Environmental Sciences, American University of Sharjah, P.O. Box 26666, Sharjah, UAE., Majdalawieh A; Department of Biology, Chemistry and Environmental Sciences, American University of Sharjah, P.O. Box 26666, Sharjah, UAE., Ramanathan M; Department of Biology, Chemistry and Environmental Sciences, American University of Sharjah, P.O. Box 26666, Sharjah, UAE., Sebastian A; Sharjah Institute for Medical Research, University of Sharjah, P.O. Box 27272, Sharjah 00000, UAE., Al-Tel TH; Sharjah Institute for Medical Research, University of Sharjah, P.O. Box 27272, Sharjah 00000, UAE.; College of Pharmacy, University of Sharjah, P.O. Box 27272, Sharjah 00000, UAE.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2021 Sep 17; Vol. 86 (18), pp. 12872-12885. Date of Electronic Publication: 2021 Sep 03.
DOI: 10.1021/acs.joc.1c01523
Abstrakt: 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.
Databáze: MEDLINE