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Visible‐Light‐Driven C−H Oxidation of Cyclic Tertiary Amines: Access to Synthetic Strychnos Alkaloids with Antiviral Activity
Author(s) -
Guryev Anton A.,
Hahn Friedrich,
Marschall Manfred,
Tsogoeva Svetlana B.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900078
Subject(s) - strychnos , chemistry , reagent , combinatorial chemistry , visible spectrum , tetrahydroisoquinoline , alkaloid , organic chemistry , materials science , optoelectronics
Air and visible light have been used in facile direct C−H oxidation of cyclic tertiary amines at ambient conditions, employing organic dyes as photocatalysts and LED. Tolerance of this new environmentally compatible protocol to various side‐chain derivatizations of tryptoline and tetrahydroisoquinoline substrates was demonstrated. The developed method provides a straightforward and sustainable route towards δ‐lactams, which feature strong antiviral properties (EC 50 down to 4.6±1.8 μ m ) against human cytomegalovirus (HCMV). The clear advantages, which are easily available and inexpensive reagents, organic dyes, visible light, air/O 2 and atom efficiency, make this system highly appealing for synthesis of versatile Strychnocarpine alkaloid derivatives with antiviral activity.