Bisannulation of 2, 3‐Dichloro‐1, 4‐naphthoquinone with o‐Nitrophenylacetic Acid Derivatives: A Succinct Synthesis of the ABCD Ring System of Alpkinidine. Issue 16 (19th April 2013)

• Record Type: Journal Article
• Authors: Buccini, Marco; Jeow, Shi Yuan; Byrne, Lindsay; Skelton, Brian W.; Nguyen, Tuan Minh; Chai, Christina L. L.; Piggott, Matthew J.
• Is Part Of: European journal of organic chemistry. Issue 16(2013)
• Page Start: 3232
• Page End: 3240
• Publication Date: 2013-04-19
• Subjects: Natural products -- Alkaloids -- Nitrogen heterocycles -- Annulation -- Synthesis design; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300227
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : An annulation strategy involving successive Michael and amino‐Michael substitution reactions of 2, 3‐dichloro‐1, 4‐naphthoquinone has been used to rapidly construct the ABCD ring system of the pyrroloacridine natural product alpkinidine.