Work

Biomimetic total synthesis of ten Securinega alkaloids

Year: 2026

Type: article

Abstract: The Securinega alkaloids are a diverse family of polycyclic alkaloids with broad biological importance. In this study, a formal [4 + 2] cycloaddition strategy has been used to complete the biomimetic total synthesis of six Securinega alkaloids, notably using biosynthetically plausible scaffold-forming steps and aqueous reaction conditions. A further four alkaloids were also generated via subsequent rearrangement reactions. Altogether, the total syntheses of ten Securinega alkaloids are described, in one or two linear steps from proposed biosynthetic precursor menisdaurilide. These results support the hypothesis that the same or similar pathways may operate in planta.

Source: White Rose Research Online (University of Leeds, The University of Sheffield, University of York)

Authors: UNSWORTH, WILLIAM PAUL, Waddell, Lachlan James Noble, Jiang, Zhouqian, GROGAN, GIDEON JAMES, Lichman, Benjamin R.

Institution: University of York

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Directorate for Biological Sciences, Biotechnology and Biological Sciences Research Council

Award: Discovery and reconstitution of securinine alkaloid biosynthesis

OpenAlex ID: W7125889135