Synthesis of Natural Product-like Polyheterocycles via One-Pot Cascade Oximation, C-H Activation, and Alkyne Annulation.
An efficient protocol for the direct transformation of chroman-4-ones to tricyclic fused pyridines with the skeleton of cassiarins, a family of alkaloids with antimalarial activity, was developed. Also, a general strategy for modular construction of polyheterocycles with diverse natural product-like skeletons was developed by using ketone-alkyne bifunctional substrates. These reactions involved a one-pot cascade oximation of ketones, rhodium-catalyzed C-H activation, and intermolecular/intramolecular alkyne annulations under mild conditions with high atom, step, and redox economy.
Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University , Beijing 100084, China.
Liyao
L
Zheng
Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University , Beijing 100084, China.
Yunhui
Y
Bin
Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University , Beijing 100084, China.
Yunpeng
Y
Wang
Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University , Beijing 100084, China.
Ruimao
R
Hua
D000480:Alkynes / Q000737:chemistry*; D000962:Antimalarials / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D006859:Hydrogen / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
D000480:Alkynes; D000962:Antimalarials; D001688:Biological Products; D006575:Heterocyclic Compounds, 3-Ring; D010091:Oximes; D002244:Carbon; D006859:Hydrogen