Tetrabenazine was synthesized in six steps from commercially available materials. The carbon framework for tetrabenazine was assembled rapidly in two steps, which involved the Michael addition of a tetrahydroisoquinoline to the Baylis-Hillman adduct of isobutyraldehyde and methyl vinyl ketone. The key step in this work, annulation of the final ring, was achieved through photoredox catalysis. Solvent choice in the photoredox cyclization was critical. Use of methanol led to the formation of a mixed ketal, whereas acetonitrile/water (10:1) led to the direct formation of the desired ketone.

Synthesis of tetrabenazine via visible light photoredox catalysis

249th National Meeting (2015)

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