DU8+ Computations Reveal a Common Challenge in the Structure Assignment of Natural Products Containing a Carboxylic Anhydride Moiety
Ivan M. Novitskiy, Andrei G. Kutateladze
Abstract
DU8+ computations of NMR spectra revealed a relatively common error in the structure assignment of carboxylic anhydride-containing natural products. Computationally driven revisions of ten of these structures are reported in this Note. The majority of the misassigned structures featured a hydroxy group that is proximal to the proposed anhydride moiety and capable of lactone formation.
Topics & Concepts
MoietyChemistryGroup (periodic table)Carboxylic acidCombinatorial chemistryOrganic chemistryStereochemistryMolecular spectroscopy and chiralityMetabolomics and Mass Spectrometry StudiesAlkaloids: synthesis and pharmacology