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Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis.

ABSTRACT: (±)-Tetrabenazine was synthesized in six steps from commercially available compounds. The key cyclization substrate was assembled rapidly via Baylis-Hillman and aza-Michael reactions. Annulation of the final ring was achieved through visible light photocatalysis, wherein carbon-carbon bond formation was driven by the oxidation of a tertiary amine. Solvent played a critical role in the photoredox cyclization outcome, whereas methanol led to a mixed ketal, acetonitrile/water (10:1) gave direct cyclization to (±)-tetrabenazine and occurred more rapidly.

SUBMITTER: Orgren LR

PROVIDER: S-EPMC4684717 | biostudies-literature | 2015 Dec

REPOSITORIES: biostudies-literature

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Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis.

Orgren Lindsey R LR Maverick Emily E EE Marvin Christopher C CC

The Journal of organic chemistry 20151113 24

(±)-Tetrabenazine was synthesized in six steps from commercially available compounds. The key cyclization substrate was assembled rapidly via Baylis-Hillman and aza-Michael reactions. Annulation of the final ring was achieved through visible light photocatalysis, wherein carbon-carbon bond formation was driven by the oxidation of a tertiary amine. Solvent played a critical role in the photoredox cyclization outcome, whereas methanol led to a mixed ketal, acetonitrile/water (10:1) gave direct cyc ...[more]

PMID: 26544155

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