A Radical Addition Approach to a Heptafluoroisopropyl Substituted Arene, Combined with a Highly Diastereoselective Annulation Reaction To Synthesize the Tricyclic Core of BMS-986251
Abstract:We
have devised an asymmetric route to the tricyclic core 10 of BMS-986251. The six-step synthesis utilizes readily
available starting materials, involves the one-step installation of
the perfluoro isopropyl moiety through a radical mechanism, and leverages
a novel diastereoselective annulation to build the pyrrolidine ring.
Overall, 10 was obtained in 49% yield as a single stereoisomer
in 6 steps and 3 isolations using this new route.
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