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- Title
Bisannulation of 2,3-Dichloro-1,4-naphthoquinone with o-Nitrophenylacetic Acid Derivatives: A Succinct Synthesis of the ABCD Ring System of Alpkinidine.
- Authors
Buccini, Marco; Jeow, Shi Yuan; Byrne, Lindsay; Skelton, Brian W.; Nguyen, Tuan Minh; Chai, Christina L. L.; Piggott, Matthew J.
- Abstract
Three bisannulation strategies have been used to rapidly construct pentacyclic benzo-fused pyrrolo[4,3,2- mn]acridines, similar to several biologically active natural products. The key steps involve Michael substitution of 2,3-dichloro-1,4-naphthoquinone with o-nitrophenylacetic acid derivatives, followed by domino amino-Michael substitutions/cyclisations. The most efficient of these syntheses provided a model compound ( 1) including the ABCD ring-system of alpkinidine, in just three steps and 55 % overall yield.
- Subjects
ANNULATION; NAPHTHOQUINONE; PHENYLACETIC acid; QUINONE derivatives; CHEMICAL derivatives; RING formation (Chemistry); NATURAL products; HETEROCYCLIC compounds
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 16, p3232
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300227