Bisannulation of 2,3‐Dichloro‐1,4‐naphthoquinone with  o ‐Nitrophenylacetic Acid Derivatives: A Succinct Synthesis of the ABCD Ring System of Alpkinidine | Zendy

Buccini Marco | Zendy; Jeow Shi Yuan | Zendy; Byrne Lindsay | Zendy; Skelton Brian W. | Zendy; Nguyen Tuan Minh | Zendy; Chai Christina L. L. | Zendy; Piggott Matthew J. | Zendy

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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.

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