Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation. (24th April 2019)

• Record Type: Journal Article
• Authors: Kutateladze, Andrei G.; Krenske, Elizabeth H.; Williams, Craig M.
• Is Part Of: Angewandte Chemie. Volume 131:Number 21(2019)
• Page Start: 7181
• Page End: 7186
• Publication Date: 2019-04-24
• Subjects: Anti-Bredt-Olefine -- Bredt-Regel -- Brückenkopf-Doppelbindungen -- Naturstoffe -- Neuzuordnungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201902777
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is a strategy for predicting the isolabilities of oxygen‐substituted bridgehead natural products based on calculations of olefin strain energies, NMR chemical shifts and coupling constants (DU8+). This approach provides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.