Arnold Robert E, Saska Jan, Mesquita-Ribeiro Raquel, Dajas-Bailador Federico, Taylor Laurence, Lewis William, Argent Stephen, Shao Huiling, Houk Kendall N, Denton Ross M
The GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham Jubilee Campus Triumph Road Nottingham NG7 2TU UK
School of Life Sciences, University of Nottingham NG7 2UH UK.
Chem Sci. 2024 Jun 19;15(30):11783-11793. doi: 10.1039/d4sc03232b. eCollection 2024 Jul 31.
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.
我们报道了西蒙索尔F（3）、西蒙索尔醇（5）、法尔吉宁（4）和大花玉兰醇（6）的首次全合成，此外还合成了西蒙索尔C（2）、西蒙索尔G（1）和厚朴酚（14）。这些合成基于鏻叶立德介导的级联反应以及天然产物异构化反应，后者通过假定生物合成二烯酮中间体的科普重排进行。作为天然产物异构化反应的一个推论，我们提出了厚朴酚（14）、西蒙索尔醇（5）和大花玉兰醇（6）的另一种生物合成途径，该途径将这个家族中的天然产物统一在一个共同的前体黄樟素（7）之下。最后，我们证明西蒙索尔C（2）和西蒙索尔F（3）能促进原代小鼠皮质神经元的轴突生长。
