Total Synthesis of Matrine Alkaloids

07 June 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The total synthesis of three diastereomeric matrine natural products is reported. The eight-step synthesis commences with simple acyclic precursors, forms all four rings of the tetracyclic natural product framework and forges ten of the twenty covalent bonds of the target structure. The chemical synthesis adopts an unprecedented strategy that encompasses both transform and stereochemical attributes. A cross-conjugated triene is positioned at the core of an acyclic branched structure, which collapses to the tetracyclic natural product framework through an orchestrated sequence of two intramolecular cycloadditions. A subsequent, late-stage hydrogenation is accompanied by strain-release redox epimerizations to deliver the three natural products. Semisynthetic manipulations of matrine provide access to ten additional natural products.


total synthesis
synthesis design

Supplementary materials

Total Synthesis of Matrine Alkaloids Supporting Information
File contains experimental procedures and characterization data for all compounds.


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