Ontology highlight
ABSTRACT:
SUBMITTER: Orgren LR
PROVIDER: S-EPMC4684717 | biostudies-literature | 2015 Dec
REPOSITORIES: biostudies-literature
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]