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Synlett 1997; 1997(10): 1187-1189
DOI: 10.1055/s-1997-983
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Practical Synthesis of the Trisubstituted Naphthalene Carboxylic Acid from Neocarzinostatin Chromophore

Mark Rucker, Reinhard Brückner*
  • *Institut für Organische Chemie, Georg-August-Universität, Tammannstr. 2, D-37077 Göttingen, Germany, Fax: +49-551-392944; e-mail: rbrueck@gwdg.de
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Publication Date:
31 December 2000 (online)

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Neocarzinostatin carboxylic acid (5) has been synthesized in 33% overall yield by a nine-step sequence which is operationally easy enough to be carried out by second-year chemistry students. 3,5-dimethylanisole was brominated in the para and in one benzylic position so that an SN2 reaction with sodium cyanide led to the cyanated aryl bromide 15. Heck-coupling with ethyl acrylate gave the α,β-unsaturated ester 14. It was converted into the saturated diester 18 through dissolving-metal reduction, saponification of nitrile and ester groups, and re-esterification with MeOH. Dieckmann cyclization and dehydroaromatization furnished ester 19 whose hydrolysis to the title compound 5 has been known.

aromatization - Dieckmann cyclization - Heck coupling - naphthalene derivative