Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 24, Pages 12635-12640Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02199
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Funding
- National Institutes of Health (NIH), National Institute of General Medical Sciences (NIGMS) [P20 GM103429]
- Research Corporation for Science Advancement [ID: 21087]
- National Science Foundation [1040470]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1040470] Funding Source: National Science Foundation
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(+/-)-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.
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