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Communication | Regular issue | Vol 23, No. 2, 1985, pp.261-264
Published online, 1st January, 1970
DOI: 10.3987/R-1985-02-0261
Formal Synthesis of Lavendamycin Methyl Ester: The Regioselective Synthesis to the Bromoquinolinequinone Systems of Key Intermediate

Satoshi Hibino,* Miko Okazaki, Masataka Ichikawa, Kohichi Sato, and Takashi Ishizu

*Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan

Abstract

We achieved a formal synthesis of lavendamycin methyl ester as follows. The Pictet-Spengler reaction of 8-benzyloxyquinolin-2-aldehyde 4 with β-methyltryptophan ethyl ester 5, gave pentacyclic β-carboline 7. Hydrogenolysis of benzyl ether 7 and bromination of 8-hydroxyquinoline 8 afforded 5,7-dibromo-8-hydroxyquinoline 11. Oxidation of bromophenol 11 by cerium ammonium nitrate proceeded regioselectively to the desired p-quinone system 13. On the other hand, the ethyl ester 8 was converted into its methyl ester 9 and led to the methyl ester of bromoquinolinequinone 14 regioselectively in the same way, that is, Kende‘s intermediate.