930285-77-1Relevant academic research and scientific papers
Catalytic C-N and C-H Bond Activation: Ortho-Allylation of Benzoic Acids with Allyl Amines
Hu, Xiao-Qiang,Hu, Zhiyong,Zhang, Guodong,Sivendran, Nardana,Goo?en, Lukas J.
supporting information, p. 4337 - 4340 (2018/07/29)
A facile insertion of ruthenium into aromatic C-H and allylic C-N bonds are the key steps in a [Ru(p-cymene)Cl2]2-catalyzed ortho-C-H allylation of benzoic acids. This protocol allows drawing on the large pool of allylic amines for state-of-the-art ortho-functionalizations of arenes, turning neutral amines into leaving groups. Concise syntheses of biologically active compounds provide further evidence of the synthetic potential of this methodology.
Zearalenone mimics: Synthesis of (E)-6-(1-Alkenyl)-substituted β-resorcylic acid esters
Mikula, Hannes,Hametner, Christian,Froehlich, Johannes
, p. 1939 - 1946 (2013/05/22)
Two versatile strategies for the synthesis of mimics of the Fusarium mycotoxin zearalenone (1) have been developed. Optimized preparation of (E)-6-(1-alkenyl) substituted β-resorcylic acid esters was realized via ortho-directed lithiation of variable substrates combined with allylation/isomerization or via formylation/Schlosser-Wittig olefination using different protective group patterns. Spontaneous decarboxylation of (E)-6-(1-alkenyl) substituted β-resorcylic acids indicated the influence of this substituent on the chemical behavior of these compounds. These mimics were already used for the development of optimized standard protocols for the synthesis of phase II metabolites of ZEN (glucosides, glucuronides), and further applications (i.e., sulfate conjugates) are still under investigation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
Synthesis of the core structure of cruentaren A
Vintonyak, Viktor V.,Maier, Martin E.
, p. 655 - 658 (2008/02/05)
The core structure of the macrolactone cruentaren A (1) was prepared via a ring-closing alkyne metathesis reaction. The corresponding ester 33 was constructed from the benzoic acid derivative 14 and the diol 30. As a key step in the synthesis of acid 14, an aldol reaction resulted in the required anti-OH/Me pattern. The anti-configuration in the stereotetrad of diol 30 was established by a Marshall reaction.
