Two unprecedented oxygenated aaptaminoids have been synthesized starting from cheap and easily available 2,3-dihydroxybenzoic acid with the satisfactory overall yields of 31% and 34%. The key step of the procedure is the divergent thermic 5-exodig vs base-promoted 6-endodig cyclization of a 5-alkynylquinolinone derivative.
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http://dx.doi.org/10.1021/jo3020598 | DOI Listing |
Chemistry
April 2022
State Key Laboratory of Coordination Chemistry and, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, 163 Xianlin Avenue, 210023, Nanjing, Jiangsu, P. R. China.
Aaptaminoids are a unique family of marine alkaloids bearing a benzo[de][1,6]-naphthyridine core. This work describes the first total synthesis of suberitines A-D (1-4), four typical dimeric natural aaptaminoids, employing a step-saving bidirectional strategy. Key methods applied in the total synthesis include a cationic cascade to construct the bis-isoquinoline(s) with Hendrickson reagent-mediated Friedel-Crafts-type cyclization and eliminative aromatization, and a Bronsted acid-promoted Vilsmeier cyclization to generate the naphthyridine(s).
View Article and Find Full Text PDFJ Org Chem
November 2012
Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica A. Marchesini, Università degli Studi di Milano, via Venezian, 21, 20133 Milano, Italy.
Two unprecedented oxygenated aaptaminoids have been synthesized starting from cheap and easily available 2,3-dihydroxybenzoic acid with the satisfactory overall yields of 31% and 34%. The key step of the procedure is the divergent thermic 5-exodig vs base-promoted 6-endodig cyclization of a 5-alkynylquinolinone derivative.
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