142012-03-1Relevant academic research and scientific papers
Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis
Trost, Barry M.,Masters, James T.,Lumb, Jean-Philip,Fateen, Dahlia
, p. 1354 - 1360 (2014)
The palladium-catalyzed oxidative desymmetrization of meso-dibenzoates yields γ-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building blocks and elaborated cycloalkanone derivatives. The ability to prepare both enantiomers of the oxidative desymmetrization products enables a unified strategy toward stereochemically diverse epoxyquinoid natural products.
Development of a β-C-H Bromination Approach toward the Synthesis of Jerantinine e
Huber, Tatjana,Preuhs, Teresa A.,Gerlinger, Christa K. G.,Magauer, Thomas
, p. 7410 - 7419 (2017/07/26)
The development of an asymmetric and highly convergent three-component synthesis of the functionalized ABC ring system of the Aspidosperma alkaloid jerantinine E is reported. The presented synthetic strategy relies on our recently developed method for the one-pot β-C-H bromination of enones, which allows for rapid construction of the tricyclic tetrahydrocarbazolone core via a palladium-catalyzed amination and oxidative indole formation. Moreover, a secondary amine building block that contains all carbon atoms of the D and E ring of the natural product could be installed in three additional steps.
