Natural Products Containing the Oxetane and Related Moieties Present Additional Challenges for Structure Elucidation: A DU8+ Computational Case Study

J Org Chem. 2019 Jun 21;84(12):7575-7586. doi: 10.1021/acs.joc.9b01005. Epub 2019 Jun 7.

Abstract

Analysis of published NMR data for natural products containing the oxetane moiety, with the help of a recently developed parametric/DFT hybrid computational method DU8+, has revealed that oxetanes and related compounds constitute yet another significant challenge in structure elucidation and stereochemistry assignment, as more than 30 structures required revision. The most common pitfalls are discussed, and revised structures are suggested for 26 natural products.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Biological Products / chemistry*
  • Density Functional Theory*
  • Ethers, Cyclic / chemistry*
  • Models, Molecular
  • Molecular Conformation

Substances

  • Biological Products
  • Ethers, Cyclic
  • oxetane