Impacts of Steric Compression, Protonation, and Intramolecular Hydrogen Bonding on the ¹⁵N NMR Spectroscopy of Norditerpenoid Alkaloids and Their Piperidine-Ring Analogues.

ABSTRACT: ¹H-¹⁵N HMBC spectra of norditerpenoid alkaloids and their synthetic azabicyclic analogues were obtained to investigate the impacts of the through-space effect of steric compression, protonation, and formation of intramolecular hydrogen bonding on the ¹⁵N NMR spectroscopy of these natural products and their piperidine-containing analogues. A rare ¹⁵N NMR effect of steric compression is demonstrated in half-cage A/E-rings of norditerpenoid alkaloid free bases and their synthetic azabicyclic analogues, in which the distribution of the lone pair of electrons of the tertiary amine N-atom is sterically restricted by bridged cycloalkanes, e.g., cyclopentane, cyclohexane, and cycloheptane rings. This results in significant changes in the ^15</

SUBMITTER: Zeng Z 

PROVIDER: S-EPMC7301575 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature