1. Transformation of (allo)securinine to (allo)norsecurinine via a molecular editing strategy.
- Author
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Kim, Seoyoung, Lee, Hee-Seung, Han, Sunkyu, Sekar, Prakash, Joo, Jung Min, Cho, Cheon-Gyu, and Kim, Sanghee
- Subjects
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PIPERIDINE , *HETEROCYCLIC compounds , *BIOSYNTHESIS , *ALKALOIDS , *FUNCTIONAL groups - 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]
- Published
- 2024
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