Concise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing.

ABSTRACT: Lycopodium alkaloid complanadine A, isolated by Kobayashi et al. in 2000, is a complex and unsymmetrical dimer of lycodine. Biologically, it is a novel and promising lead compound for the development of new treatment for neurodegenerative disorders and persistent pain management. Herein, we reported a concise synthesis of complanadine A using a pyrrole-to-pyridine molecular editing strategy. The use of a nucleophilic pyrrole as the precursor of the desired pyridine enabled an efficient and one-pot construction of the tetracyclic core skeleton of complanadine A and lycodine. The pyrrole group was then converted to a 3-chloropyridine via the Ciamician-Dennstedt one carbon ring expansion. A subsequent C-H arylation between the 3-chloropyridine and a pyridine N-oxide formed the u

SUBMITTER: Martin BS 

PROVIDER: S-EPMC11636943 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature