Kudashev Anton, Vergura Stefania, Zuccarello Marco, Bürgi Thomas, Baudoin Olivier
University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056, Basel, Switzerland.
University of Geneva, Department of Physical Chemistry, 30 Quai Ernest-Ansermet, 1211, Geneva 4, Switzerland.
Angew Chem Int Ed Engl. 2024 Jan 2;63(1):e202316103. doi: 10.1002/anie.202316103. Epub 2023 Nov 30.
The divergent synthesis of two indane polyketides of the indidene family, namely (±)-indidene A (11 steps, 1.7 %) and (+)-indidene C (13 steps, 1.3 %), is reported. The synthesis of the trans-configured common indane intermediate was enabled by palladium(0)-catalyzed methylene C(sp )-H arylation, which was performed in both racemic and enantioselective (e.r. 99 : 1) modes. Further elaboration of this common intermediate by nickel-catalyzed dehydrogenative coupling allowed the rapid installation of the aroyl moiety of (±)-indidene A. In parallel, the biphenyl system of (±)- and (+)-indidene C was constructed by Suzuki-Miyaura coupling. These investigations led us to revise the structures of indidenes B and C.
报道了茚二烯家族两种茚满聚酮化合物的发散合成，即（±）-茚二烯A（11步，产率1.7%）和（+）-茚二烯C（13步，产率1.3%）。通过钯（0）催化的亚甲基C（sp）-H芳基化反应实现了反式构型的常见茚满中间体的合成，该反应以消旋和对映选择性（对映体比例为99∶1）两种模式进行。通过镍催化的脱氢偶联对该常见中间体进行进一步修饰，能够快速引入（±）-茚二烯A的芳酰基部分。同时，通过铃木-宫浦偶联反应构建了（±）-和（+）-茚二烯C的联苯体系。这些研究使我们对茚二烯B和C的结构进行了修正。
