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 Mai 2024
Accepted
13 Jun 2024
First published
19 Jun 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

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