Genzink Matthew J, Rossler Matthew D, Recendiz Herman, Yoon Tehshik P
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
J Am Chem Soc. 2023 Sep 6;145(35):19182-19188. doi: 10.1021/jacs.3c07132. Epub 2023 Aug 21.
Pseudodimeric cyclobutanes constitute a large class of natural products that could, in principle, be efficiently synthesized via [2+2] photocycloadditions. However, the difficulty in developing chemo-, regio-, diastereo-, and enantioselective cycloadditions has limited their use in asymmetric syntheses. Herein, we show that chiral acid catalysts promote highly selective visible-light photocycloadditions, the products of which can be quickly transformed into truxinate natural products. This general approach has enabled the synthesis of both dimeric and pseudodimeric cyclobutane natural products with excellent enantioselectivity.
假二聚体环丁烷构成了一大类天然产物,原则上可以通过[2+2]光环加成反应高效合成。然而,开发化学、区域、非对映和对映选择性光环加成反应的困难限制了它们在不对称合成中的应用。在此,我们表明手性酸催化剂能促进高度选择性的可见光光环加成反应,其产物可快速转化为吐昔酸天然产物。这种通用方法能够以优异的对映选择性合成二聚体和假二聚体环丁烷天然产物。