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Transformation of (allo)securinine to (allo)norsecurinine via a molecular editing strategy.
- Source :
-
Frontiers in Chemistry . 2024, p1-5. 5p. - Publication Year :
- 2024
-
Abstract
- Securinega alkaloids have intrigued chemists since the isolation of securinine in 1956. This family of natural products comprises a securinane subfamily with a piperidine substructure and norsecurinane alkaloids featuring a pyrrolidine core. From a biosynthetic perspective, the piperidine moiety in securinane alkaloids derives from lysine, whereas the pyrrolidine moiety in norsecurinane natural products originates from ornithine, marking an early biogenetic divergence. Herein, we introduce a single-atom deletion strategy that enables the late- stage conversion of securinane to norsecurinane alkaloids. Notably, for the first time, this method enabled the transformation of piperidine-based (allo) securinine into pyrrolidine-based (allo)norsecurinine. Straightforward access to norsecurinine from securinine, which can be readily extracted from the plant Flueggea suffruticosa, abundant across the Korean peninsula, holds promise for synthetic studies of norsecurinine-based oligomeric securinega alkaloids. [ABSTRACT FROM AUTHOR]
- Subjects :
- *PIPERIDINE
*HETEROCYCLIC compounds
*BIOSYNTHESIS
*ALKALOIDS
*FUNCTIONAL groups
Subjects
Details
- Language :
- English
- ISSN :
- 22962646
- Database :
- Academic Search Index
- Journal :
- Frontiers in Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 175402931
- Full Text :
- https://doi.org/10.3389/fchem.2024.1355636