Premium
Bisannulation of 2,3‐Dichloro‐1,4‐naphthoquinone with o ‐Nitrophenylacetic Acid Derivatives: A Succinct Synthesis of the ABCD Ring System of Alpkinidine
Author(s) -
Buccini Marco,
Jeow Shi Yuan,
Byrne Lindsay,
Skelton Brian W.,
Nguyen Tuan Minh,
Chai Christina L. L.,
Piggott Matthew J.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300227
Subject(s) - chemistry , ring (chemistry) , domino , yield (engineering) , michael reaction , naphthoquinone , stereochemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy , catalysis
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.