Issue 20, 2023

Re-examining the stereochemistry of polycyclic suffruticosine via TDDFT calculations, ECD spectroscopy, and chemical synthesis

Abstract

The determination of complex natural product structures involves two main steps: (1) establishing atom connectivity, and (2) assigning stereochemistry. While the former step is now routinely accomplished using 1H and 13C NMR data, supplemented with various 2D NMR experiments, assigning relative and absolute stereochemistry to complex natural products continues to present a significant challenge. In this study, we employ time-dependent density functional theory (TDDFT) computations to analyze electronic circular dichroism (ECD) spectra and elucidate the structure of polycyclic suffruticosine. By combining TDDFT-assisted ECD spectral assignment with experimental ECD spectra obtained from the eastern fragment (securinine and allosecurinine) and the chemically synthesized western fragment of suffruticosine, we demonstrate that the true structure of natural suffruticosine is the enantiomer of the initially reported structure in the isolation paper.

Graphical abstract: Re-examining the stereochemistry of polycyclic suffruticosine via TDDFT calculations, ECD spectroscopy, and chemical synthesis

Supplementary files

Article information

Article type
Research Article
Submitted
16 юли 2023
Accepted
28 авг 2023
First published
30 авг 2023

Org. Chem. Front., 2023,10, 5123-5129

Re-examining the stereochemistry of polycyclic suffruticosine via TDDFT calculations, ECD spectroscopy, and chemical synthesis

T. Kim, S. Kim, G. Chung, K. Park and S. Han, Org. Chem. Front., 2023, 10, 5123 DOI: 10.1039/D3QO01098H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements