Issue 30, 2024

Total synthesis, biological evaluation and biosynthetic re-evaluation of Illicium-derived neolignans

Abstract

We report the first total syntheses of simonsol F (3), simonsinol (5), fargenin (4), and macranthol (6) in addition to syntheses of simonsol C (2), simonsol G (1), and honokiol (14). The syntheses are based upon a phosphonium ylide-mediated cascade reaction and upon natural product isomerization reactions which proceed through Cope rearrangements of putative biosynthetic dienone intermediates. As a corollary of the natural product isomerization reactions, we propose an alternative biosynthesis of honokiol (14), simonsinol (5), and macranthol (6) which unites the natural products in this family under a single common precursor, chavicol (7). Finally, we demonstrate that simonsol C (2) and simonsol F (3) promote axonal growth in primary mouse cortical neurons.

Graphical abstract: Total synthesis, biological evaluation and biosynthetic re-evaluation of Illicium-derived neolignans

Supplementary files

Article information

Article type
Edge Article
Submitted
17 মে 2024
Accepted
13 জুন 2024
First published
19 জুন 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 11783-11793

Total synthesis, biological evaluation and biosynthetic re-evaluation of Illicium-derived neolignans

R. E. Arnold, J. Saska, R. Mesquita-Ribeiro, F. Dajas-Bailador, L. Taylor, W. Lewis, S. Argent, H. Shao, K. N. Houk and R. M. Denton, Chem. Sci., 2024, 15, 11783 DOI: 10.1039/D4SC03232B

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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