A solution- and solid-phase approach to tetrahydroquinoline-derived polycyclics having a 10-membered ring.
With the goal of library generation using a polycyclic derivative 5 having an enamide functional group, a simple and practical, enantioselective synthesis of tetrahydroquinoline derivative 2 was achieved. The phenolic hydroxyl group in compound 2 was utilized as an anchoring site for solid-phase synthesis. The ring closing metathesis approach yielded the desired polycyclic product 5 on solid phase in five steps (overall 40% yield). Compound 5 is a novel scaffold for the library generation of natural product-like polycyclics having a functionalized medium ring for obtaining a new class of small molecules to be utilized as chemical probes.
Khadem
Shahriar
S
Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Canada K1N 6N5.
Joseph
Reni
R
Rastegar
Majid
M
Leek
Donald M
DM
Oudatchin
Kostantin A
KA
Arya
Prabhat
P