Bisannulation of 2,3‐Dichloro‐1,4‐naphthoquinone with o ‐Nitrophenylacetic Acid Derivatives: A Succinct Synthesis of the ABCD Ring System of Alpkinidine
2013; Wiley; Volume: 2013; Issue: 16 Linguagem: Inglês
10.1002/ejoc.201300227
ISSN1434-193X
AutoresMarco R. Buccini, Shi Yuan Jeow, Lindsay T. Byrne, Brian W. Skelton, Tuan Minh Nguyen, Christina L. L. Chai, Matthew Piggott,
Tópico(s)Synthesis and Biological Activity
ResumoAbstract 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.
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